A revision of the positive sign of the optical rotation and its maximum value of α-eudesmol

• Published in: Phytochemistry (Oxford) Vol. 52; no. 4; pp. 689 - 694
• Main Authors: Toyota, Masao, Yonehara, Yumiko, Horibe, Isao, Minagawa, Kazuyuki, Asakawa, Yoshinori
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Ltd 01-10-1999; Elsevier
• Subjects: (−)-α-Eudesmol; Absolute configuration; alcohols; Biological and medical sciences; chemical constituents of plants; Chemical constitution; chemical structure; Fundamental and applied biological sciences. Psychology; Liverwort; Maximum optical rotation; molecular conformation; mosses and liverworts; optical rotation; Plant physiology and development; Porella perrottetiana; Sesquiterpene alcohol; sesquiterpenoids; Japan; Maximum optical rotation; (−)-α-Eudesmol; Liverwort; Porella perrottetiana; Sesquiterpene alcohol; Absolute configuration; Molecular structure; Sesquiterpenes; Bryophyta; Alcohol; Optical purity; Hepaticae
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/S0031-9422(99)00299-X

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.