Total Synthesis of the Cytotoxic Macrocycle (+)-Hitachimycin

Amos B. Smith; Thomas A. Rano; Noritaka Chida; Gary A. Sulikowski; John L. Wood

doi:10.1021/ja00047a008

Total Synthesis of the Cytotoxic Macrocycle (+)-Hitachimycin

Amos B. Smith, Thomas A. Rano, Noritaka Chida, Gary A. Sulikowski, John L. Wood

Research output: Contribution to journal › Article › peer-review

17 Citations (Scopus)

Abstract

The first total synthesis of the antitumor antibiotic (+)-hitachimycin (a.k.a. stubomycin) (1) has been achieved in 22 steps and 1.1% overall yield. The cornerstone of the synthetic strategy was a highly stereoselective three-component coupling of (-)-5-methoxycyclopentenone (4) with a zincate derived from vinyl iodide 3a and aldehyde (-)-51.

Original language	English
Pages (from-to)	8008-8022
Number of pages	15
Journal	Journal of the American Chemical Society
Volume	114
Issue number	21
DOIs	https://doi.org/10.1021/ja00047a008
Publication status	Published - 1992 Oct 1
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja00047a008

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abstract = "The first total synthesis of the antitumor antibiotic (+)-hitachimycin (a.k.a. stubomycin) (1) has been achieved in 22 steps and 1.1% overall yield. The cornerstone of the synthetic strategy was a highly stereoselective three-component coupling of (-)-5-methoxycyclopentenone (4) with a zincate derived from vinyl iodide 3a and aldehyde (-)-51.",

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AU - Rano, Thomas A.

AU - Chida, Noritaka

AU - Sulikowski, Gary A.

AU - Wood, John L.

PY - 1992/10/1

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Total Synthesis of the Cytotoxic Macrocycle (+)-Hitachimycin

Abstract

ASJC Scopus subject areas

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