Studies toward the Total Synthesis of GKK1032A2, a Structurally Unique Anti­tumor Compound: Stereoselective Construction of the Tricarbocyclic System

Noriyoshi Arai; Hideaki Ui; Satoshi Omura; Isao Kuwajima

doi:10.1055/s-2005-871549

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Synlett 2005(11): 1691-1694
DOI: 10.1055/s-2005-871549

LETTER

Studies toward the Total Synthesis of GKK1032A₂, a Structurally Unique Antitumor Compound: Stereoselective Construction of the Tricarbocyclic System

Noriyoshi Arai^a, Hideaki Ui^b, Satoshi Omura^c, Isao Kuwajima*^a
^a Creation and Function of New Molecules and Molecular Assemblies, Core Research for Evolutional Science and Technology (CREST), Japan Science and Technology Agency (JST), 1-15-1 Kitasato, Sagamihara, Kanagawa 228-8555, Japan
Fax: +81(42)7789931; e-Mail: kuwajima@lisci.kitasato-u.ac.jp;
^b School of Pharmaceutical Science, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan
^c The Kitasato Institute, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8642, Japan

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Publication History

Received 15 April 2005
Publication Date:
14 June 2005 (online)

Abstract
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Abstract

The unique tricarbocyclic system in GKK1032A₂, an antitumor agent from Penicillium sp. GKK1032, was constructed in a highly stereoselective manner, starting from a readily available Hajos-Wiechert ketone analog.

Key words

antitumor agents - carbocycles - Diels-Alder reactions - natural products - stereoselective synthesis

References

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Crystallographic data for 22: formula, C₃₇H₆₀O₂Si; FW, 612.94; crystal system, orthorhombic; space group, P2₁2₁2₁; a = 11.7726 (4) Å, b = 12.9543 (4) Å, c = 23.5023 (8) Å; V = 3584.2 (2) Å³; Z = 4; T = 170 K; D _calcd = 1.136 g cm^-1; λ(MoK _α) = 0.71070 Å; R1 = 0.0418 [I>2σ(Ι)]; wR2 = 0.1082; GOF(F ²) = 1.064.