Asymmetric total synthesis of natural (-)-and unnatural (+)-steganacin: Determination of the absolute configuration of natural antitumor steganacin

K Tomioka, T Ishiguro, Y Iitaka, K Koga

Index: Tomioka, Kiyoshi; Ishiguro, Tsuneo; Iitaka, Yoichi; Koga, Kenji Tetrahedron, 1984 , vol. 40, # 8 p. 1303 - 1312

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Citation Number: 106

Abstract

A virtually complete asymmetric control in the synthesis of 2, 3-disubstituted butan-4-olide (10) was demonstrated by employing the butenolide (12) as the chiral acceptor for the conjugate 1, 4-addition. Highly efficient asymmetric total synthesis of natural (-)-and unnatural (+)-steganacin was accomplished. The absolute stereostructure of natural antitumor steganain was determined to be 1.