Enantioselective synthesis of a diastereomer of iriomoteolide-1a. What is the correct structure of the natural product?
An enantioselective approach to a diastereomer of iriomoteolide-1a is described. Highlighted is a SmI(2)-mediated intramolecular reductive cyclization approach to complex cyclic hemiketals. An acetylide-chloroformate coupling strategy is also featured. Our results show that the structures of iriomoteolide-1a-1c require careful reassessment.
Fang
Lijing
L
Department of Chemistry, Texas A&M University, College Station, Texas 77843-3255, USA.
Yang
Jiong
J
Yang
Fei
F
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000970:Antineoplastic Agents; D001688:Biological Products; D018942:Macrolides; C520799:iriomoteolide-1a