Asymmetric total synthesis of bacillariolide III, a marine oxylipin.
[reaction: see text] The asymmetric total synthesis of bacillariolide III has been achieved via 15 linear steps in 14.6% overall yield. The key feature of this synthetic route involves the highly stereoselective construction of the vinyl-substituted bicyclic lactone by an intramolecular Pd(0)-catalyzed allylic alkylation and its facile conversion to the hydroxy bicyclic lactone skeleton of bacillariolide III, induced by stereoselective vinylcerium addition to the aldehyde. In addition, the (Z)-pentenoic acid was efficiently introduced by the internal hydroxy group tethered ring-closing metathesis (RCM).
Seo
Seung-Yong
SY
College of Pharmacy, Seoul National University, Seoul 151-742, Korea.
Jung
Jae-Kyung
JK
Paek
Seung-Mann
SM
Lee
Yong-Sil
YS
Kim
Seok-Ho
SH
Lee
Kwang-Ok
KO
Suh
Young-Ger
YG
D000447:Aldehydes / Q000737:chemistry; D000818:Animals; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D017377:Diatoms / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D019086:Bridged Bicyclo Compounds, Heterocyclic; D007783:Lactones; C485138:bacillariolide III