Synthetic transformations of higher terpenoids: VIII. [4+2]-cycloaddition reactions of lambertianic acid

Synthetic transformations of higher terpenoids: VIII. [4+2]-cycloaddition reactions of lambertianic acid Full article

Journal

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

Output data

Year: 2003, Volume: 39, Number: 1, Pages: 57-74 Pages count : 18 DOI: 10.1023/A:1023490528591

Authors

Kharitonov YV ¹ , Shults EE ¹ , Shakirov MM ¹ , Tolstikov GA ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, Novosibirsk Organ Chem Inst, Siberian Div, Novosibirsk 630090, Russia

The Diels-Alder reaction of lambertianic acid with maleic anhydride occurred in a stereoselective fashion and yielded diastereoisomeric (1R,2S,6R,7R)- and (1S,2R,6S,7S)-exo-adducts. The latter reacted with L-valinol to give the corresponding diterpenoid imides, 4-aza-9-oxabicyclo[2.2.1]dec-8-enes. Reactions of lambertianic acid with N-substituted maleimides in the presence of Lewis acids afforded diastereoisomeric adducts having both exo and endo configuration. Some transformations of the adducts were examined with a view to obtain cantharidin and dihydroisoindole analogs.

Kharitonov Y. , Shults E. , Shakirov M. , Tolstikov G.
Synthetic transformations of higher terpenoids: VIII. [4+2]-cycloaddition reactions of lambertianic acid
Russian Journal of Organic Chemistry. 2003. V.39. N1. P.57-74. DOI: 10.1023/A:1023490528591 WOS Scopus РИНЦ

Харитонов Ю.В. , Шульц Э.Э. , Шакиров М.М. , Толстиков Г.А.
Синтетические трансформации высших терпеноидов viii.* реакция [4+2]-циклоприсоединения ламбертиановой кислоты
Журнал органической химии (RUSS J ORG CHEM+). 2003. Т.39. №1. С.67-84. РИНЦ

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