Total synthesis of (+)-Brefeldin A.
The total synthesis of (+)-brefeldin A has been accomplished via 15 linear steps in a 7.9% overall yield from the known Weinreb amide 6. The key parts of this approach include the stereoselective construction of the cis-disubstituted hydroxycyclopentane skeleton and the direct introduction of the C1-C3 acrylate moiety using a new variant of a trans-vinylogous acyl anion equivalent.
Suh
Young-Ger
YG
College of Pharmacy, Seoul National University, San 56-1, Shinlim-Dong, Kwanak-Gu 151-742, Korea. ygsuh@plaza.snu.ac.kr
Jung
Jae-Kyung
JK
Seo
Seung-Yong
SY
Min
Kyung-Hoon
KH
Shin
Dong-Yun
DY
Lee
Yong-Sil
YS
Kim
Seok-Ho
SH
Park
Hyun-Ju
HJ
D000577:Amides / Q000737:chemistry*; D000838:Anions / Q000737:chemistry; D020126:Brefeldin A / Q000031:analogs & derivatives / Q000032:analysis / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C465980:4-oxo-brefeldin A; D000577:Amides; D000838:Anions; D020126:Brefeldin A