Alkylated Levoglucosan in Organic Synthesis. : A Formal Total Synthesis of Elaiophylin

Hideo NAKAMURA; Kazushi ARATA; Takeshi WAKAMATSU; Yoshio BAN; Masakatsu SHIBASAKI

doi:10.1248/cpb.38.2435

Hideo NAKAMURA, Kazushi ARATA, Takeshi WAKAMATSU, Yoshio BAN, Masakatsu SHIBASAKI

Author information

Keywords: corn starch, levoglucosan, epoxide, trans-diaxial opening, nucleophile, lactonization, chiral synthesis

JOURNAL FREE ACCESS

1990 Volume 38 Issue 9 Pages 2435-2441

DOI https://doi.org/10.1248/cpb.38.2435

Details

Abstract

Levoglucosan (8) has been found to be a useful material for the synthesis of chiral compounds having five contiguous chiral centers (14). Conversion of 8 to 14 involves two trans-diaxial openings of epoxides by nucleophilic reagents. Among 14, 14c was successfully transformed into the intermediate 5 for the total synthesis of elaiophylin (1). Efficient lactonization of the carboxylic acid 33 has been achieved by use of Yamaguchi's method.

Corresponding author

Register with J-STAGE for free!