Premium
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)
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom