乙卯研究所

全合成天然有機化合物

構造式集 （1/10）(±)-Nominine

NAngew. Chem. Int. Ed., 43, 4646-4649 (2004).
有機合成化学協会誌, 64(3), 237-250 (2006).
Tetrahedron, 62, 7056-7070 (2006).
Tetrahedron, 62, 7071-7092 (2006).
Tetrahedron, 62, 7093-7112 (2006).

OHH
H

Natural (+)-Duocarmycin SA
OMe

1st generation: Chem. Pharm. Bull., 44, 67-79 (1996).
2nd generation: Chem. Pharm. Bull., 44, 1631-1633 (1996).
OMe
2nd generation: Chem. Pharm. Bull., 46, 400-412 (1998).
OMe
3rd generation: Chem. Pharm. Bull., 46, 559-571 (1998).

NMeOOCN
HNO H
O(±)- and Unnatural (-)-Duocarmycin SA
1st generation: Tetrahedron Lett., 35, 2573-2576 (1994).
3rd generation: Chem. Pharm. Bull., 43, 1064-1066 (1995).
OMe 1st generation: Chem. Pharm. Bull., 44, 67-79 (1996).
OMe
2nd generation: Chem. Pharm. Bull., 44, 1631-1633 (1996).
2nd generation: Chem. Pharm. Bull., 46, 400-412 (1998).
OMeN
MeOOC

N
HNO H
O

(±)-EpibatidineHNNCl

Chem. Pharm. Bull., 42, 1432-1436 (1994).

H

Natural (+)-Hapalindole OOHHNCSHChem. Pharm. Bull., 42, 1393-1398 (1994).

NH

Unnatural (+)-Herbindole A

NH

Tetrahedron Lett., 33, 4595-4598 (1992).
Chem. Pharm. Bull., 42, 854-864 (1994).

Unnatural (+)-Herbindole BN
H

Tetrahedron Lett., 33, 4595-4598 (1992).
Chem. Pharm. Bull., 42, 854-864 (1994).

乙卯研究所

全合成天然有機化合物

構造式集 （2/10）

Unnatural (+)-Herbindole C

Tetrahedron Lett., 33, 4595-4598 (1992).
Chem. Pharm. Bull., 42, 854-864 (1994).

N
H

Natural (+)- and (±)-cis-Trikentrin B

Tetrahedron, 46, 4179-4192 (1990).
Tetrahedron Lett., 34, 4815-4818 (1993).
Chem. Pharm. Bull., 42, 854-864 (1994).

N
H

Unnatural (+)- and (±)-trans-Trikentrin B

Tetrahedron, 46, 4179-4192 (1990).
Tetrahedron Lett., 34, 4815-4818 (1993).
Chem. Pharm. Bull., 42, 854-864 (1994).

N
H

Unnatural (+)- and (±)-iso-trans-Trikentrin B

Tetrahedron, 46, 4179-4192 (1990).
Tetrahedron Lett., 34, 4815-4818 (1993).
Chem. Pharm. Bull., 42, 854-864 (1994).

NH(S)-(-)- and (±)-Pindolol
HNHOHO

Chem. Pharm. Bull., 40, 2353-2357 (1992).
Chem. Pharm. Bull., 40, 2358-2361 (1992).

N
H(±)-Tetrahydropseudodistomine
OHNH2
N
H

Heterocycles, 33, 349-356 (1992).

(±)-Hapalindole H
H
H

H
NH

NC

Tetrahedron, 46, 6351-6360 (1990).

乙卯研究所

全合成天然有機化合物

構造式集 （3/10）(±)-Hapalindole U
H
H

H

NC

Tetrahedron, 46, 6351-6360 (1990).

N
H

Unnatural (-)- and (±)-cis-Trikentrin A

Tetrahedron Lett., 30, 5771-5772 (1989).
Tetrahedron, 46, 4179-4192 (1990).

N
H

Unnatural (-)- and (±)-trans-Trikentrin AN
HTetrahedron Lett., 30, 5771-5772 (1989).
Tetrahedron, 46, 4179-4192 (1990).

(±)-Hapalindole J
H
H

H

NC

Tetrahedron Lett., 30, 1815-1818 (1989).
Tetrahedron, 46, 6331-6342 (1990).

N
H(±)-Hapalindole M
HHH

NCS

Tetrahedron Lett., 30, 1815-1818 (1989).
Tetrahedron, 46, 6331-6342 (1990).

N
H

Natural (-)-Pendolmycin
Me

N

HHH
N
O

OH

N
H

Tetrahedron, 46, 5113-5120 (1990).
Tetrahedron, 47, 7615-7624 (1991).
Tetrahedron, 47, 8545-8558 (1991).

7-(3-Methyl-2-butenyl)indole
N
H

Heterocycles, 29, 771-782 (1989).

乙卯研究所

全合成天然有機化合物

構造式集 （4/10）

6-(3-Methyl-2-butenyl)indoleNH

Heterocycles, 29, 771-782 (1989).

Natural (-)-Teleocidin B-3
MeN

HHH
NO

OH

Chem. Pharm. Bull, 37, 563-564 (1989).
Tetrahedron, 47, 8559-8572 (1991).

NH

Natural (-)-Teleocidin B-4
MeN

HH H
N

OH

O

Chem. Pharm. Bull, 37, 563-564 (1989).
Tetrahedron, 47, 8559-8572 (1991).

N
H(±)-Kopsinine (R=H, formal syn.) ; (±)-Pleiocarpinine (R=Me, formal syn.)(±)-Aspidofractine (R=CHO, formal syn.) ; (±)-Pleiocarpine (R=COOMe, formal syn.)
N H
NR

H
COOMe

Tetrahedron Lett., 28, 3985-3986 (1987).

(±)-Kopsanone (R=H, formal syn.); (±)-N-ethylkopsanone (R=Me, formal syn.)
N H
ONTetrahedron Lett., 28, 3985-3986 (1987).

R

Lyngbyatoxin A (= Teleocidin A-1)
MeN

HH H
NOH
O
N
H

Tetrahedron Lett., 28, 2265-2268 (1987).
Tetrahedron, 47, 8545-8558 (1991).

Teleocidin A-2
MeN

HH H
NOH
O
N
H

Tetrahedron Lett., 28, 2265-2268 (1987).
Tetrahedron, 47, 8545-8558 (1991).

乙卯研究所

全合成天然有機化合物

構造式集 （5/10）(±)-α-Cyclopiazonic Acid
HHO

NOH

HO

Heterocycles, 23, 1111-1117 (1985).

N
H(±)-Sedinine
HOHOH

H
N
MeHeterocycles, 23, 831-834 (1985).

(±)-Palustrine
HOH
N

N
H
HON
H

H

Chem. Pharm. Bull., 32, 812-814 (1984).
Chem. Pharm. Bull., 32, 3789-3791 (1984).

(±)-Vindorosine (formal syn.)
N

H

OH
N
OAc
H
Me COOMe

Chem. Pharm. Bull., 32, 2477-2479 (1984).

(±)-Cannabisativine
HOH
N

N
H
HO

H

OH
H

N
H

Tetrahedron Lett., 25, 969-972 (1984).

(±)-Clavicipitic Acid I
H H H
COOH
N

N
H

Heterocycles, 20, 1963-1968 (1983).

(±)-Clavicipitic Acid II
H H H
COOH
N

N
H

Heterocycles, 20, 1963-1968 (1983).

乙卯研究所

全合成天然有機化合物

構造式集 （6/10）(±)-Sedacryptine
HO O

H OHMeNH H
MeHeterocycles, 22, 601-605 (1983).

(±)-Dihydrosetoclavine
OHMe

MeN H

H

Heterocycles, 16, 375-379 (1981).
Heterocycles, 16, 1481-1486 (1981).

N
H(±)-Prosophylline
HOHO

ON
H

Heterocycles, 16, 973-977 (1981).

(±)-Festuclavine
HMeMeN H

H

unpublished data

NH(±)-Costaclavine
HMeMeN H

H

unpublished data
NH(±)-Pyroclavine
HMeMeN HHunpublished data

N
H(±)-Nupharolutine
MeH
N
H
O

MeOH

Heterocycles, 15, 237-240 (1981).

乙卯研究所

全合成天然有機化合物

構造式集 （7/10）(±)-Chanolavine I
NHMe
H

HO
H

Heterocycles, 16, 375-379 (1981).

N
H(±)-Chanolavine IINHMe
HHOH

unpublished dataN
H(±)-6,7-Secoagroclavine
NHMe
H
H

Heterocycles, 14, 1101-1105 (1980).
N
H(±)-Pseudocarpamic Acid
HOCOOHNH

Me

Heterocycles, 14, 615-618 (1980).

(±)-Prosafrinine
HOMeO
N
H

Heterocycles, 14, 615-618 (1980).

(±)-3-Epiuleine
MeN

H
NHH

Tetrahedron Lett., 21, 839-840 (1980).
H(±)-Carpamic Acid
HOMeNH

COOH

Heterocycles, 14, 169-173 (1980).

乙卯研究所

全合成天然有機化合物

構造式集 （8/10）(±)-Azimic Acid
HOCOOHNH

Me

Heterocycles, 14, 169-173 (1980).

(±)-4-(3-Methyl-2-butenyl)tryptophan (formal syn.)
NH2
COOH

Tetrahedron Lett., 1979, 3477-3480.

N
H(±)-1-O-Methyl-5-benzamido-5-deoxyallopiperidinose
OHOH

HON
HOOMe

Chem. Pharm. Bull., 26, 3364-3372 (1978).

Bz(±)-1-O-Methyl-5-benzamido-5-deoxyaltropiperidinose
OHOHHONHOOMe

Chem. Pharm. Bull., 26, 3364-3372 (1978).

Bz(±)-5-Amino-5-deoxyribose deriv. and (±)-5-Amino-5-deoxylyxose deriv.
OAc

OAc

OAc

OAc AcO

AcO

NN

OMe
COOMe

OMe
COOMe

Chem. Pharm. Bull., 26, 2188-2197 (1978).

(±)-1-O-Methyl-5-benzamido-5-deoxy-dl-idopiperidinose
OHOH

HON
HOOMe

Chem. Pharm. Bull., 24, 2657-2660 (1976).

Bz(±)-5-Methoxycarbonyl-5-deoxy-dl-xylopiperidinose tetraacetate
OAc
OAc

AcO
NOAc
COOMe

Chem. Pharm. Bull., 24, 2651-2656 (1976).

乙卯研究所

全合成天然有機化合物

構造式集 （9/10）(±)-1-O-Methyl-N-benzoyl-dl-nojirimycin
OHOH

HON
HOOMe

Chem. Pharm. Bull., 23, 2567-2572 (1975).

Bz

Ungeremine III Methobromide
OMeO
N+Br-O

Tetrahedron Lett., 1974, 1179-1180.

(±)-Elaeocarpine
HON

MeH
H

Tetrahedron Lett., 1971, 4395-4398.

O

HalfordinolNO
HO

Tetrahedron Lett., 1971, 4393-4394.

N

Flavopereirine (formal syn.)

N+N
H

unpublished data(±)-Physovenine (formal syn.)
MeH
N

MeOO

NMeOH

Tetrahedron Lett., 1971, 4391-4392.

(±)-Anisessine
ON
COOEt

NHN

Tetrahedron Lett., 1971, 4387-4390.

乙卯研究所

全合成天然有機化合物

構造式集 （10/10）(±)-Vasicinone
ONNOH

Tetrahedron Lett., 1971, 4387-4390.

Withasomnine

N N

Tetrahedron Lett., 1968, 5711-5714.