Novel approach for the introduction of a C‐1 oxygenated group on the decalin skeleton: first asymmetric total synthesis of 1 S ,6 S ‐dihydroxy‐eudesm‐3‐ene | Zendy

Zheng Guojun | Zendy; Chen Jinchun | Zendy; Fang Lijing | Zendy; Guan Yukun | Zendy; Li Yulin | Zendy

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Novel approach for the introduction of a C‐1 oxygenated group on the decalin skeleton: first asymmetric total synthesis of 1 S ,6 S ‐dihydroxy‐eudesm‐3‐ene

Author(s) -

Zheng Guojun,

Chen Jinchun,

Fang Lijing,

Guan Yukun,

Li Yulin

Publication year - 2004

Publication title -

chirality

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.43

H-Index - 77

eISSN - 1520-636X

pISSN - 0899-0042

DOI - 10.1002/chir.20062

Subject(s) - chemistry , decalin , total synthesis , stereochemistry , aldol reaction , skeleton (computer programming) , natural product , ring (chemistry) , group (periodic table) , organic chemistry , catalysis , computer science , programming language

This paper describes a novel approach for the introduction of a C‐1 hydroxyl on the decalin ring system, starting from (−)‐carvone. Utilizing the substratecontrolled Mukaiyama aldol reaction and alkaline cyclization as key steps, the C‐1 oxygenated decalin eudesmane skeleton 2 ′ and its four isomers were synthesized efficiently. Furthermore, X‐ray structural analysis showed that the claimed structure for the natural product is incorrect. Chirality 16:483–485, 2004. © 2004 Wiley‐Liss, Inc.

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