Total synthesis and structural revision of the marine macrolide neopeltolide

Daniel W. Custar; Thomas P. Zabawa; Karl A. Scheidt

doi:10.1021/ja710080q

Total synthesis and structural revision of the marine macrolide neopeltolide

Daniel W. Custar, Thomas P. Zabawa, Karl A. Scheidt^*

^*Corresponding author for this work

Chemistry

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

127 Scopus citations

Abstract

The total synthesis and structural revision of the marine natural product neopeltolide is reported. The key bond-forming step involves a Lewis acid-catalyzed intramolecular cyclization to install the tetrahydropyran ring and the macrocycle simultaneously. This type of cyclization is the first of its kind and assembles the carbon backbone of the natural product efficiently. The synthesis of the reported structure revealed differences in the data between the natural and synthetic material. After significant investigation, the diastereomeric molecule with the C11 and C13 configurations inverted was synthesized using the initial route. This compound matches the data reported for neopeltolide (¹H, ¹³C, HRMS, IR, NOESY, [α]), thereby establishing the correct overall structure for this potent macrolide natural product, including the relative and absolute stereochemistry.

Original language	English (US)
Pages (from-to)	804-805
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	130
Issue number	3
DOIs	https://doi.org/10.1021/ja710080q
State	Published - Jan 23 2008

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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abstract = "The total synthesis and structural revision of the marine natural product neopeltolide is reported. The key bond-forming step involves a Lewis acid-catalyzed intramolecular cyclization to install the tetrahydropyran ring and the macrocycle simultaneously. This type of cyclization is the first of its kind and assembles the carbon backbone of the natural product efficiently. The synthesis of the reported structure revealed differences in the data between the natural and synthetic material. After significant investigation, the diastereomeric molecule with the C11 and C13 configurations inverted was synthesized using the initial route. This compound matches the data reported for neopeltolide (1H, 13C, HRMS, IR, NOESY, [α]), thereby establishing the correct overall structure for this potent macrolide natural product, including the relative and absolute stereochemistry.",

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AU - Custar, Daniel W.

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AU - Scheidt, Karl A.

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AB - The total synthesis and structural revision of the marine natural product neopeltolide is reported. The key bond-forming step involves a Lewis acid-catalyzed intramolecular cyclization to install the tetrahydropyran ring and the macrocycle simultaneously. This type of cyclization is the first of its kind and assembles the carbon backbone of the natural product efficiently. The synthesis of the reported structure revealed differences in the data between the natural and synthetic material. After significant investigation, the diastereomeric molecule with the C11 and C13 configurations inverted was synthesized using the initial route. This compound matches the data reported for neopeltolide (1H, 13C, HRMS, IR, NOESY, [α]), thereby establishing the correct overall structure for this potent macrolide natural product, including the relative and absolute stereochemistry.

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Total synthesis and structural revision of the marine macrolide neopeltolide

Abstract

ASJC Scopus subject areas

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