New Olefinic Cyclizations by Oxymetallation. Conversion of (−)‐elemol to (−)‐selina‐4α, 11‐diol (cryptomeridiol) and (−)‐guai‐1 (10)‐ene‐4α, 11‐diol | Zendy

Renold Walter | Zendy; Ohloff Günther | Zendy; Norin Torbjörn | Zendy

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New Olefinic Cyclizations by Oxymetallation. Conversion of (−)‐elemol to (−)‐selina‐4α, 11‐diol (cryptomeridiol) and (−)‐guai‐1 (10)‐ene‐4α, 11‐diol

Author(s) -

Renold Walter,

Ohloff Günther,

Norin Torbjörn

Publication year - 1979

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19790620409

Subject(s) - chemistry , diol , lithium aluminium hydride , ene reaction , organic chemistry , camphor , stereochemistry

Acetoxythallation of (−)‐elemol acetate ( 1b ) yields a diacetate 2b which after treatment with lithium aluminium hydride gives (−)‐guai‐1 (10)‐ene‐4α, 11‐diol ( 2a ). (−)‐Elemol ( 1a ) is converted to (−)‐selina‐4α, 11‐diol ( 9 , cryptomeridiol) by hydroxymercuration followed by reductive demercuration. (+)‐γg‐Elemene ( 5 ) similarly yields (+)‐selin‐7(11)‐en‐4α‐ol ( 11 , juniper camphor). The stereochemistry and mechanism of these metal salt‐induced olefinic cyclization and their biogenetic implication are discussed.

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