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An Efficient Ruthenium‐Catalyzed Formal Synthesis of (−)‐Isoavenaciolide
Author(s) -
Labeeuw Olivier,
Blanc Delphine,
Phansavath Phannarath,
RatovelomananaVidal Virginie,
Genêt JeanPierre
Publication year - 2004
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.200400047
Subject(s) - chemistry , ruthenium , ketone , stereocenter , formal synthesis , stereoselectivity , catalysis , stereochemistry , sequence (biology) , combinatorial chemistry , organic chemistry , enantioselective synthesis , biochemistry
A formal synthesis of (−)‐isoavenaciolide ( 1 ) by two different routes is reported. The first approach, leading to a key precursor 2 of (−)‐isoavenaciolide ( 1 ), features the stereoselective construction of the three contiguous stereogenic centers by Evans diastereoselective reduction ( d . e . = 80%) of β‐hydroxy ketone 8 . In the more efficient second approach, the nine‐step sequence leading to the key precursor 2 involves sequential ruthenium‐catalyzed hydrogenation reactions of β‐keto ester 4 and β‐hydroxy ketone 14 to form the two hydroxyl groups with an excellent control of the anti stereochemistry ( d . e . = 99%). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)