NOC Approach to Spiroketals. A Total Synthesis of (±)-Talaromycin B

Alan P. Kozikowski; James G. Scripko

doi:10.1021/ja00314a018

NOC Approach to Spiroketals. A Total Synthesis of (±)-Talaromycin B

Alan P. Kozikowski, James G. Scripko

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Abstract

A total synthesis of the unqiue spiroketal natural product talaromycin B (1) is reported. This molecule, produced in nature by the toxicogenic fungus Talaromyces stipitatus, was constructed in the laboratory from the isoxazoline 6 generated (Figure presented.) on reacting the oxime 4 with the olefin 5 in the presence of NaOCl/Et₃N/H₂O/CH₂Cl₂. The synthesis scheme is sufficiently flexible and efficient so as to be of practical use in the preparation of suitable quantities of this material for biological evaluation.

Original language	English (US)
Pages (from-to)	353-355
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	106
Issue number	2
DOIs	https://doi.org/10.1021/ja00314a018
State	Published - 1984
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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abstract = "A total synthesis of the unqiue spiroketal natural product talaromycin B (1) is reported. This molecule, produced in nature by the toxicogenic fungus Talaromyces stipitatus, was constructed in the laboratory from the isoxazoline 6 generated (Figure presented.) on reacting the oxime 4 with the olefin 5 in the presence of NaOCl/Et3N/H2O/CH2Cl2. The synthesis scheme is sufficiently flexible and efficient so as to be of practical use in the preparation of suitable quantities of this material for biological evaluation.",

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year = "1984",

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AU - Kozikowski, Alan P.

AU - Scripko, James G.

PY - 1984

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AB - A total synthesis of the unqiue spiroketal natural product talaromycin B (1) is reported. This molecule, produced in nature by the toxicogenic fungus Talaromyces stipitatus, was constructed in the laboratory from the isoxazoline 6 generated (Figure presented.) on reacting the oxime 4 with the olefin 5 in the presence of NaOCl/Et3N/H2O/CH2Cl2. The synthesis scheme is sufficiently flexible and efficient so as to be of practical use in the preparation of suitable quantities of this material for biological evaluation.

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NOC Approach to Spiroketals. A Total Synthesis of (±)-Talaromycin B

Abstract

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