Cyclization of Cembrane Diterpenoids: VIII. Acid-catalyzed Cyclization of Isocembrol

Cyclization of Cembrane Diterpenoids: VIII. Acid-catalyzed Cyclization of Isocembrol Full article

Journal

Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393

Output data

Year: 1997, Volume: 33, Number: 2, Pages: 194-204 Pages count : 11

Authors

Shpatov A.V. ¹ , Shakirov M.M. ¹ , Gatilov Yu.V. ¹ , Rybalova T.V. ¹ , Raldugin V.A. ¹

Affiliations

1	(Scopus) Novosibirsk Inst. of Organ. Chem., Siberian Division, Russian Academy of Sciences, pr. Lavrent'eva 9, Novosibirsk, 630090, Russian Federation

The structure was established of all oxygen-containing compounds produced in the reaction of isocembrol, the diterpene alcohol, with aqueous formic acid in chloroform. During this cyclization, unlike the case of cembrene cyclization described previously, an earlier unknown reaction pathway is realized that results in a new stereochemical group of products with the carbon skeleton of 2,11-cyclocembrane. The presence of steric hindrances to rotation of the Δ7 double-bond moiety in the ten-membered cycle of these compounds is responsible for their existence in solutions in the form of two slowly interconverting conformers.

Shpatov A.V. , Shakirov M.M. , Gatilov Y.V. , Rybalova T.V. , Raldugin V.A.
Cyclization of Cembrane Diterpenoids: VIII. Acid-catalyzed Cyclization of Isocembrol
Russian Journal of Organic Chemistry. 1997. V.33. N2. P.194-204. Scopus РИНЦ

Shpatov A.V. , Shakirov M.M. , Gatilov Y.V. , Rybalova T.V. , Raldugin V.A.
Cyclization of cembrane diterpenoids .8. Acid-catalyzed cyclization of isocembrole
Журнал органической химии (RUSS J ORG CHEM+). 1997. V.33. N2. P.224-235. WOS

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