123123-38-6Relevant articles and documents
A revision of the positive sign of the optical rotation and its maximum value of α-eudesmol
Toyota, Masao,Yonehara, Yumiko,Horibe, Isao,Minagawa, Kazuyuki,Asakawa, Yoshinori
, p. 689 - 694 (1999)
The ether extract of the liverwort Porella perrottetiana afforded (-)- α-eudesmol, which showed an opposite sign of the optical rotation to that found in higher plants. Present work on the absolute configuration and an optical purity of (-)-α-eudesmol strongly suggested that the positive values (e.g. + 28.5°) described in many previous papers should be revised. Since the absolute configuration of (-)-α-eudesmol was identical to that of (+)- β-eudesmol found in the higher plants, it was apparent that the expression of the positive sign might be revised to (-)-α-eudesmol. The optical purity, reconfirmation of the absolute configuration and synthesis of (-)-α-eudesmol will be discussed.
Jain,McCloskey
, p. 5139 (1972)
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