Premium
First Total Synthesis of (±)‐13‐Hydroxyneocembrene
Author(s) -
Xing Yacheng,
Cen Wen,
Lan Jiong,
Li Ying,
Li Yulin
Publication year - 1999
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199900082
Subject(s) - chemistry , total synthesis , stereochemistry
First total synthesis of (±)‐13‐hydroxyneocembrene ( 1 ), starting from 6‐methyl‐5‐hepten‐2‐one ( 6 ) and geraniol ( 7 ), is described. The key steps are (i) the addition of sulfur‐stabilized carbanion 12 to aldehyde 9 , (ii) the synthesis of 18 by using phase‐transfer catalyzed coupling reaction, and (iii) low‐valent titanium‐induced intramolecular coupling of oxo aldehyde 3 to afford the target molecule after the final deprotection.