page_title: Phorbol
section_title: Total synthesis
hierarchical_section_title: Phorbol / Total synthesis
caption_attribution_description: English: Overview of phorbol synthesis
context_page_description: Phorbol is a natural, plant-derived organic compound. It is a member of the tigliane family of diterpenes. Phorbol was first isolated in 1934 as the hydrolysis product of croton oil, which is derived from the seeds of the purging croton, Croton tiglium. The structure of phorbol was determined in 1967.
  Various esters of phorbol have important biological properties, the most notable of which is the capacity to act as tumor promoters through activation of protein kinase C. They mimic diacylglycerols, glycerol derivatives in which two hydroxyl groups have reacted with fatty acids to form esters. The most common and potent phorbol ester is 12-O-tetradecanoylphorbol-13-acetate, also called phorbol-12-myristate-13-acetate, which is used as a biomedical research tool in contexts such as models of carcinogenesis.
context_section_description: A total synthesis of enantiopure phorbol was developed in 2015.  While this synthesis will not replace natural isolation products, it will enable researchers to create phorbol analogs for use in research, especially creating phorbol derivatives that can be evaluated for anti-cancer activity.  Previously, the difficulty with synthesizing phorbol had been creating C–C bonds, especially in the six-membered ring at the top of the molecule.  This synthesis starts from (+)-3-carene, and uses a series of 19 steps to eventually create (+)-phorbol.
caption: Overview of the complete synthesis of (+)-phorbol starting with (+)-3-carene
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