Complex sentence: He was appointed commander of "Bounty" on 16 August 1787, with orders to enter the Pacific by rounding Cape Horn and then, after collecting the breadfruit plants, sail westward through the Endeavour Strait and across the Indian and Atlantic Oceans to the West Indies.
Split into simpler sentences: He was appointed commander of "Bounty" on 16 August 1787. His orders were to enter the Pacific via Cape Horn and then, after collecting the breadfruit plants, sail westward through the Endeavour Strait and across the Indian and Atlantic Oceans to the West Indies.