Synthesis of (-)-okilactomycin by a prins-type fragment-assembly strategy

Jason M. Tenenbaum; William J. Morris; Daniel W. Custar; Karl A. Scheidt

doi:10.1002/anie.201102037

Synthesis of (-)-okilactomycin by a prins-type fragment-assembly strategy

Jason M. Tenenbaum, William J. Morris, Daniel W. Custar, Karl A. Scheidt

Chemistry

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

34 Scopus citations

Abstract

All things converge: A highly convergent synthesis of (-)-okilactomycin utilizes a Prins-type Maitland-Japp cyclization for the fragment assembly of two complex intermediates (see scheme). The synthesis also employs a highly diastereoselective Lewis acid promoted Diels-Alder reaction and an olefin ring-closing metathesis to close a strained 11-membered macrocycle.

Original language	English (US)
Pages (from-to)	5892-5895
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	26
DOIs	https://doi.org/10.1002/anie.201102037
State	Published - Jun 20 2011

Keywords

Maitland-Japp reaction
Prins reaction
natural products
tetrahydropyrans
total synthesis

ASJC Scopus subject areas

General Chemistry
Catalysis

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10.1002/anie.201102037

Cite this

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abstract = "All things converge: A highly convergent synthesis of (-)-okilactomycin utilizes a Prins-type Maitland-Japp cyclization for the fragment assembly of two complex intermediates (see scheme). The synthesis also employs a highly diastereoselective Lewis acid promoted Diels-Alder reaction and an olefin ring-closing metathesis to close a strained 11-membered macrocycle.",

keywords = "Maitland-Japp reaction, Prins reaction, natural products, tetrahydropyrans, total synthesis",

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AU - Tenenbaum, Jason M.

AU - Morris, William J.

AU - Custar, Daniel W.

AU - Scheidt, Karl A.

PY - 2011/6/20

Y1 - 2011/6/20

N2 - All things converge: A highly convergent synthesis of (-)-okilactomycin utilizes a Prins-type Maitland-Japp cyclization for the fragment assembly of two complex intermediates (see scheme). The synthesis also employs a highly diastereoselective Lewis acid promoted Diels-Alder reaction and an olefin ring-closing metathesis to close a strained 11-membered macrocycle.

AB - All things converge: A highly convergent synthesis of (-)-okilactomycin utilizes a Prins-type Maitland-Japp cyclization for the fragment assembly of two complex intermediates (see scheme). The synthesis also employs a highly diastereoselective Lewis acid promoted Diels-Alder reaction and an olefin ring-closing metathesis to close a strained 11-membered macrocycle.

KW - Maitland-Japp reaction

KW - Prins reaction

KW - natural products

KW - tetrahydropyrans

KW - total synthesis

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Synthesis of (-)-okilactomycin by a prins-type fragment-assembly strategy

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 816131: Experimental Crystal Structure Determination

Cite this

Synthesis of (-)-okilactomycin by a prins-type fragment-assembly strategy

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 816131: Experimental Crystal Structure Determination

Cite this