Enantioselective Construction of the C1-C16 Segment of Lasonolide A

Tatsuya Deba; Fumika Yakushiji; Mitsuru Shindo; Kozo Shishido

doi:10.1055/s-2003-40856

LETTER

Enantioselective Construction of the C₁-C₁₆ Segment of Lasonolide A

Tatsuya Deba, Fumika Yakushiji, Mitsuru Shindo, Kozo Shishido*
Institute for Medicinal Resources, University of Tokushima, 1-78 Sho-machi, Tokushima 770-8505, Japan
Fax: +81(88)6339575; e-Mail: shishido@ph2.tokushima-u.ac.jp;

Abstract

All articles of this category

Abstract

An efficient and enantiocontrolled synthesis of the C₁-C₁₆ segment of lasonolide A has been accomplished starting from a readily available optically pure aldehyde.

Key words

natural products - cytotoxic activity - asymmetric synthesis - macrocycles - pyran

Full Text

References

<A NAME="RU07903ST-1">1</A> McConnell OJ. Horton PA. Longley RE. J. Am. Chem. Soc. 1994, 116: 6015

<A NAME="RU07903ST-2">2</A> Lee E. Song HY. Kang JW. Kim DS. Jung CK. Joo JM. J. Am. Chem. Soc. 2002, 124: 384

<A NAME="RU07903ST-3">3</A> Lee E. Song HY. Kang JW. Kim DS. Jung CK. Joo JM. Hong CY. Jeong SW. Jeon K. Bioorg. Med. Chem. Lett. 2002, 12: 3519

<A NAME="RU07903ST-4">4</A> For a review, see: Paterson I. Cowden CJ. Org. React. 1998, 51: 1

<A NAME="RU07903ST-5">5</A> Sharpless KB. Katsuki T. J. Am. Chem. Soc. 1980, 102: 5974

<A NAME="RU07903ST-6">6</A> Hirai Y. Chintani M. Yamazaki T. Momose T. Chem. Lett. 1989, 1449

<A NAME="RU07903ST-7">7</A> Sharpless KB. Katsuki T. Lee AWM. Martin PMVS. Masamune S. J. Org. Chem. 1982, 47: 1378

<A NAME="RU07903ST-8">8</A> Martin JC. Dess DB. J. Am. Chem. Soc. 1991, 113: 7277

<A NAME="RU07903ST-9">9</A> Oppolzer W. Blagg J. Rodriguez I. Walther E. J. Am. Chem. Soc. 1990, 112: 2767

<A NAME="RU07903ST-10">10</A> Still WC. J. Am. Chem. Soc. 1978, 100: 1481

<A NAME="RU07903ST-11">11</A> Paquette LA. Barriault L. Pissarnitski D. Johnston JN. J. Am. Chem. Soc. 2000, 122: 619

<A NAME="RU07903ST-12">12</A> Ando K. J. Org. Chem. 1998, 63: 8411

<A NAME="RU07903ST-13">13</A> Jorgenson MK. Leung T. J. Am. Chem. Soc. 1968, 90: 3769