Total synthesis of (+)-discodermolide: a highly convergent fourth-generation approach.
[structure: see text] A highly convergent, fourth-generation total synthesis of (+)-discodermolide (1), with a longest linear sequence of 17 steps and an overall yield of 9.0%, has been achieved. Highlighting the strategy is the efficient construction and sequential, bidirectional union of a linchpin comprising the C(9)-C(14) Wittig salt-vinyl iodide (-)-18. Importantly, Wittig salt generation proceeded in excellent yield under ambient pressure.
Smith
Amos B
AB
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.edu
Freeze
B Scott
BS
Xian
Ming
M
Hirose
Tomoyasu
T
D000473:Alkanes / Q000138:chemical synthesis*; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D002219:Carbamates / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000473:Alkanes; D000970:Antineoplastic Agents; D002219:Carbamates; D007783:Lactones; D011753:Pyrones; C071229:discodermolide