CONFORMATIONAL-ANALYSIS OF THE 10-HYDROXY AND 13-HYDROXY DERIVATIVES OF CEMBRENE

CONFORMATIONAL-ANALYSIS OF THE 10-HYDROXY AND 13-HYDROXY DERIVATIVES OF CEMBRENE Full article

Journal

Journal of Organic Chemistry
ISSN: 0022-3263

Output data

Year: 1995, Volume: 60, Number: 1, Pages: 63-69 Pages count : 7 DOI: 10.1021/jo00106a015

Authors

Vorobjev A.V. ¹ , Shakirov M.M. ¹ , Raldugin V.A. ¹ , Heathcock C.H. ²

Affiliations

1	N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of Siberian Branch of Russian Academy of Sciences
2	University of California at Berkeley, Berkeley, California, 94720

Conformational analysis of 10- and 13-hydroxycembrenes 4, 5, 7, and 8 has been carried out using NMR methods and molecular mechanics calculations. The results indicate that the conformational states of all investigated compounds in solution are characterized by the same orientation of double bonds with respect to the average plane of the macrocycle. Alcohols 4 and 8 are conformationally homogeneous, and their solution conformations correspond to the known solution (and crystal) conformation of cembrene (1). In the case of alcohols 5 and 7, there is additional conformational flexibility in the C(8)-C(11) molecular fragment. The influence of simple substituent (hydroxy group) effects and an intramolecular OH* pi-hydrogen bond on conformational states of the cembranoids are discussed.

Vorobjev A.V. , Shakirov M.M. , Raldugin V.A. , Heathcock C.H.
CONFORMATIONAL-ANALYSIS OF THE 10-HYDROXY AND 13-HYDROXY DERIVATIVES OF CEMBRENE
Journal of Organic Chemistry. 1995. V.60. N1. P.63-69. DOI: 10.1021/jo00106a015 WOS Scopus OpenAlex

Published print:	Jan 1, 1995
Published online:	May 1, 2002

Web of science:	WOS:A1995QC16000014
Scopus:	2-s2.0-0013513108
OpenAlex:	W2017544947

DB	Citing
Web of science	4
Scopus	4
OpenAlex	4