Spongistatin synthetic studies. An efficient, second-generation construction of an advanced ABCD intermediate.
[reaction: see text] A short, efficient, and stereocontrolled synthesis of (-)-4, an advanced ABCD subunit of the spongistatins, has been achieved. Central to the synthetic strategy is the multicomponent linchpin union of silyl dithianes with epoxides to access both the AB and CD fragments. Fragment coupling was then achieved via an efficient stereoselective aldol reaction. The linear sequence required 22 steps and proceeded in 4.0% overall yield.
Smith
Amos B
AB
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.edu
Doughty
Victoria A
VA
Sfouggatakis
Chris
C
Bennett
Clay S
CS
Koyanagi
Jyunichi
J
Takeuchi
Makoto
M
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D018942:Macrolides; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism; D000095702:Polyether Toxins
D000970:Antineoplastic Agents; D004988:Ethers, Cyclic; D007783:Lactones; D018942:Macrolides; C083856:spongistatin 1; D000095702:Polyether Toxins