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Synthetic transformation of santonin into (5α,7α,11β)‐3,6‐dioxogermacr‐1‐en‐13,7‐olide, a new intermediate for germacranes and guaianes
Author(s) -
Harapanhalli Ravi S.
Publication year - 1988
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198819881016
Subject(s) - chemistry , transformation (genetics) , chemical transformation , stereochemistry , organic chemistry , biochemistry , gene
A seven‐step synthesis of a new intermediate (5α,7α,11β)‐3,6‐dioxogermacr‐1‐en‐13,7‐olide ( 10 ) is described starting from (−)‐α‐santonin ( 1 ). The key step in the transformation was photolytic skeletal rearrangement of (4α,5β,6α,11β)‐5‐hydroxy‐2‐oxoeudesman‐13,6‐olide ( 9 ) to the title compounds, sensitised by mercuric oxide and iodine.