473-16-5Relevant articles and documents
Unified Approach to ent -Eudesmane-Type Terpenoid Synthesis: Total Synthesis of Sinupol and Eutyscoparin A
Ota, Koichiro,Kamaike, Kazuo,Miyaoka, Hiroaki
, p. 689 - 696 (2021/10/29)
ent-Eudesmane-type terpenoids constitute a large class of natural products derived from plants, animals, and bacteria. We describe a synthetic approach to two ent-eudesmane-type terpenoids, sinupol and eutyscoparin A, that relies on a key π-facial-and endo/exoselective intramolecular Diels Alder reaction to set the C-5 C-10 stereotriads. Further key transformations of trans-fused decalin include conversion to methyl ketone via a versatile thioester intermediate and appropriate functionalization toward target compounds.
Ilicic Acid as a Natural Quiron for the Efficient Preparation of Bioactive α- and β-Eudesmol
Barrero, Alejandro F.,Herrador, M. Mar,Arteaga, Pilar,Catalan, Julieta V.
experimental part, p. 3589 - 3594 (2009/12/01)
An efficient procedure for the isolation of the sesquiterpene ilicic acid (3) on a multigram scale of extracts obtained from aerial parts of Inula viscosa (Asteraceae) was developed. Acid 3 is an appropriate starting material for short, enantio-specific s
Stereoselective total synthesis of (-)-α-eudesmol, a P/Q-type calcium channel blocker
Aoyama,Araki,Konoike
, p. 1452 - 1454 (2007/10/03)
Practical and stereoselective total synthesis of (-)-αeudesmol 1, a P/Q-type calcium channel blocker, has been achieved with the key step being a cyclopropane ring opening accompanying introduction of a hydroxyl group. (+)-Carissone is used as a key intermediate.