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Synthesis of 12‐Methyl‐13‐tridecanolide
Author(s) -
Stanchev Stephan,
Hesse Manfred
Publication year - 1987
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.19870700519
Subject(s) - chemistry , ring (chemistry) , nitro , alcohol , medicinal chemistry , stereochemistry , organic chemistry , alkyl
The title compound was prepared from 2‐nitrocyclodecanone ( 2 ). Compound 2 was treated with 2‐methylpro‐penal to give the Michael ‐addition product 3 which was reduced to the alcohol 5 and the latter ring‐enlarged with Bu 4 NF to 12‐methyl‐10‐nitro‐13‐tridecanolide ( 6 ) followed by reductive elimination of the NO 2 group by Bu 3 SnH.