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First Synthesis of (+)‐2,14‐Deoxyalatol from α‐Santonin
Author(s) -
Xia WuJiong,
Sun LiangDong,
Shi Lei,
Zhang ShuYu,
Tu YongQiang
Publication year - 2004
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20040220412
Subject(s) - chemistry , epoxide , stereoselectivity , tetrahydrofuran , double bond , stereochemistry , ring (chemistry) , key (lock) , combinatorial chemistry , catalysis , organic chemistry , solvent , ecology , biology
A novel and general approach for synthesis of the multi‐oxygenated dihydrofuran sesquiterpenes has been developed starting from santonin. The key steps involve: the strategic acid‐catalyzed double‐bond shifting affording 4, the novel base‐promoted epoxide rearrangement of 5 generating two key functionals (the C5‐OH and the Δ 7,11 double bond), and the stereoselective cyclization of tetrahydrofuran ring without pre‐controlling the stereochemistry of C‐7. As an example of this approach, synthesis of (+)‐2,14‐deoxyalatol was described in detail.