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Bicyclo[3.2.1]octenones as Building Blocks in Natural Product Synthesis (IV): Formal Synthesis of (±)‐Hydroxyloganin Aglucone
Author(s) -
Chang ChiPeng,
Yin WeiKung,
Chang NeinChen
Publication year - 1994
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.199400084
Subject(s) - chemistry , formal synthesis , potassium hydroxide , natural product , bicyclic molecule , ring (chemistry) , product (mathematics) , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , geometry , mathematics
A formal synthesis of (±)‐hydroxyloganin aglucone from bicyclo[3.2.1]octenone 1 is described. Ring opening of syn ‐8‐(methanesulfonyloxy)‐1‐phenylthiotricyclo[4.2.1.0 3,7 ]non‐4‐en‐2‐one 14 with potassium hydroxide is the key reaction.