Spongistatin synthetic studies. evolution of a scalable synthesis for the EF fragment of (+)-Spongistatin 1 exploiting a Petasis-Ferrier union/rearrangement tactic.
[structure: see text] An efficient, stereocontrolled, and scalable second-generation synthesis of (+)-3, an advanced EF subtarget for the total synthesis of (+)-spongistatin 1, has been achieved. Highlights of the strategy include preparation of the F-ring pyran via a Petasis-Ferrier union/rearrangement sequence and installation of the chlorodiene side chain employing a cyanohydrin alkylation. The longest linear sequence, 26 steps, proceeds in 8.3% overall yield.
Smith
Amos B
AB
Department of Chemistry, Monell Chemical Senses Center, and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
Sfouggatakis
Chris
C
Gotchev
Dimitar B
DB
Shirakami
Shohei
S
Bauer
David
D
Zhu
Wenyu
W
Doughty
Victoria A
VA
D000818:Animals; D002384:Catalysis; D003500:Cyclization; D007202:Indicators and Reagents; D018942:Macrolides / Q000032:analysis / Q000138:chemical synthesis*; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism; D000095702:Polyether Toxins
D007202:Indicators and Reagents; D018942:Macrolides; C083856:spongistatin 1; D000095702:Polyether Toxins