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Synthesis 2002(14): 1979-1986
DOI: 10.1055/s-2002-34381
PAPER
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Synthesis of 1-Aminopentadecane-3,5,7,9,11,13,15-heptols and of 1,15-Diaminopentadecane-3,5,7,9,11,13-hexols and Derivatives

Sandrine Gerber-Lemaire*, Florence Popowycz, Cécile Glanzmann, Pierre Vogel
Institut de chimie moléculaire et biologique, Ecole Polytechnique Fédérale, Lausanne, Switzerland
Fax: + 41(21)6939375; e-Mail: pierre.vogel@epfl.ch;
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Publication History

Received 7 June 2002
Publication Date:
26 September 2002 (online)

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Abstract

Starting from 2,2′-methylenedifuran, enantiomeri­cally enriched (98%) (3R,5S,7R,9S,11R,13R)- and (3R,5S,7S,9R,11R,13R)-15-amino-5,7,9,11-tetrahydroxy-3,13-bis-(4-methoxybenzoyloxy)pentadec-1-yl) pivalate were prepared as well as (3R,5R,7R,9R,11S,13S)-1,15-diamino-5,7,9,11-tetra­hydroxypentadeca-3,13-diyl bis(4-methoxybenzoate) and (3R,5S,7S,9S,11R,13S)-1,15-diaminopentadecane-3,5,7,9,11,13-hexol.

Key words

aminopolyketide - asymmetric synthesis - diamino­polyketide - long-chain aminopolyols - 2,2′-methylenedifuran