108888-69-3Relevant academic research and scientific papers
Stereocontrolled synthesis of (+)-acuminolide and determination of its absolute configuration
Furuichi, Noriyuki,Kato, Mariko,Katsumura, Shigeo
, p. 1247 - 1248 (1999)
As a demonstration for an easy supply of the enantiomerically pure intermediate for the synthesis of labdane diterpenoids, stereocontrolled synthesis of (+)-acuminolide was achieved, and its absolute configuration was determined.
Common synthetic strategy for optically active cyclic terpenoids having a 1,1,5-trimethyl-trans-decalin nucleus: Syntheses of (+)-acuminolide, (-)-spongianolide A, and (+)-scalarenedial
Furuichi, Noriyuki,Hata, Toshiyuki,Soetjipto, Hartati,Kato, Mariko,Katsumura, Shigeo
, p. 8425 - 8442 (2007/10/03)
We have developed a simple and practical method for providing enantiomerically pure bi-, tri-, and tetracyclic frameworks having a 1,1,5-trimethyl-trans-decalin nucleus, and demonstrated their utility for terpenoid synthesis. Thus, we achieved the stereocontrolled total syntheses of (+)-acuminolide as a bicyclic, (-)-spongianolide A as a tricyclic, and (+)-scalarenedial as a tetracyclic terpenoid from the corresponding optically pure cyclic β-ketoesters, which were obtained by repeating the same method of the ring construction, including the olefin cyclization with Lewis acid, followed by simple optical resolution using chiral auxiliaries for acetal formation, respectively. This is a general and valuable strategy for the synthesis of enantiomerically pure cyclic terpenoids having the 1,1,5-trimethyl-trans-decalin nucleus.
Lewis Acid and Photochemically Mediated Cyclization of Olefinic β-Keto Esters
White, James D.,Skeean, Richard W.,Trammell, Gary L.
, p. 1939 - 1948 (2007/10/02)
Olefinic β-keto esters 8, 17, and 20, prepared by either carbomethoxylation of the parent ketone or alkylation of the dianion of methyl acetoacetate with the allylic bromide, underwent cyclization with stannic chloride in dichloromethane to give mono- and
