Concise syntheses of (+)-macrosphelides A and B.
[reaction: see text]. Unified and highly convergent total syntheses of (+)-macrosphelides A and B are described. Key features of the syntheses include (1) concise synthesis of the optically active delta-hydroxy-gamma-keto alpha,beta-unsaturated acid fragment via the direct addition of a trans-vinylogous ester anion equivalent to the readily available Weinreb amide and (2) facile construction of the 16-membered macrolide core of the macrosphelide series via an intramolecular nitrile-oxide cycloaddition (INOC).
Paek
Seung-Mann
SM
College of Pharmacy, Seoul National University, Korea.
Seo
Seung-Yong
SY
Kim
Seok-Ho
SH
Jung
Jong-Wha
JW
Lee
Yong-Sil
YS
Jung
Jae-Kyung
JK
Suh
Young-Ger
YG
D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis; D018942:Macrolides / Q000138:chemical synthesis*; D003904:Mitosporic Fungi / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D006571:Heterocyclic Compounds; D018942:Macrolides; C097798:macrosphelide A; C097799:macrosphelide B