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Towards the Total Synthesis of the Norsesterterpene Diacarnoxide C
Author(s) -
Schneider MarcAndré,
Seifert Karlheinz
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700922
Subject(s) - moiety , chemistry , sulfone , aldehyde , peroxide , total synthesis , stereochemistry , coupling reaction , organic chemistry , catalysis
The synthesis of the norsesterterpene diacarnoxide C was achieved. The endoperoxide moiety could be prepared in nine and the norsesquiterpene moiety in five steps starting from ( E )‐3‐methyl‐6‐oxohex‐2‐en‐1‐yl acetate and dihydro‐β‐ionone. The peroxide aldehyde and the norsesquiterpene sulfone were coupled in an ( E )‐selective Julia–Kocienski reaction. The coupling product was transformed in three additional steps to an inseparable mixture of diacarnoxide C and three further isomers.