Strategies for the formation of tetrahydropyran rings in the synthesis of natural products

P A  Clarke; S  Santos

doi:10.1002/ejoc.200500964

Strategies for the formation of tetrahydropyran rings in the synthesis of natural products

P A Clarke, S Santos

Chemistry

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

Abstract

This microreview surveys the literature over the last five years with regard to construction of functionalised tetrahydropyran (THP) rings in the context of the synthesis of natural products. The overview given is intended to provide a working knowledge of the area for those who are unfamiliar, and to refresh and remind those who do work in the area of the exciting developments in the field. While the construction of the THP rings in a number of natural products has been reviewed, we have attempted to highlight the different strategies by focusing on two natural products, namely phorboxazole and centrolobine as case studies. Over the last five years, these natural products have become a test bed for new methods for the construction of THP rings.

Original language	English
Pages (from-to)	2045-2053
Number of pages	9
Journal	European Journal of Organic Chemistry
Issue number	9
DOIs	https://doi.org/10.1002/ejoc.200500964
Publication status	Published - 28 Apr 2006

Keywords

tetrahydropyran
total synthesis
natural products
MAITLAND-JAPP REACTION
TRANSANNULAR CONJUGATE ADDITION
PHORBOXAZOLE-B
PRINS CYCLIZATION
APICULAREN-A
STEREOSELECTIVE-SYNTHESIS
REGIOSELECTIVE SYNTHESIS
HEXACYCLINIC ACID
LASONOLIDE-A
ONE-POT

Access to Document

10.1002/ejoc.200500964

Cite this

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title = "Strategies for the formation of tetrahydropyran rings in the synthesis of natural products",

abstract = "This microreview surveys the literature over the last five years with regard to construction of functionalised tetrahydropyran (THP) rings in the context of the synthesis of natural products. The overview given is intended to provide a working knowledge of the area for those who are unfamiliar, and to refresh and remind those who do work in the area of the exciting developments in the field. While the construction of the THP rings in a number of natural products has been reviewed, we have attempted to highlight the different strategies by focusing on two natural products, namely phorboxazole and centrolobine as case studies. Over the last five years, these natural products have become a test bed for new methods for the construction of THP rings.",

keywords = "tetrahydropyran, total synthesis, natural products, MAITLAND-JAPP REACTION, TRANSANNULAR CONJUGATE ADDITION, PHORBOXAZOLE-B, PRINS CYCLIZATION, APICULAREN-A, STEREOSELECTIVE-SYNTHESIS, REGIOSELECTIVE SYNTHESIS, HEXACYCLINIC ACID, LASONOLIDE-A, ONE-POT",

author = "Clarke, {P A} and S Santos",

year = "2006",

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doi = "10.1002/ejoc.200500964",

language = "English",

pages = "2045--2053",

journal = "European Journal of Organic Chemistry",

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AU - Clarke, P A

AU - Santos, S

PY - 2006/4/28

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N2 - This microreview surveys the literature over the last five years with regard to construction of functionalised tetrahydropyran (THP) rings in the context of the synthesis of natural products. The overview given is intended to provide a working knowledge of the area for those who are unfamiliar, and to refresh and remind those who do work in the area of the exciting developments in the field. While the construction of the THP rings in a number of natural products has been reviewed, we have attempted to highlight the different strategies by focusing on two natural products, namely phorboxazole and centrolobine as case studies. Over the last five years, these natural products have become a test bed for new methods for the construction of THP rings.

AB - This microreview surveys the literature over the last five years with regard to construction of functionalised tetrahydropyran (THP) rings in the context of the synthesis of natural products. The overview given is intended to provide a working knowledge of the area for those who are unfamiliar, and to refresh and remind those who do work in the area of the exciting developments in the field. While the construction of the THP rings in a number of natural products has been reviewed, we have attempted to highlight the different strategies by focusing on two natural products, namely phorboxazole and centrolobine as case studies. Over the last five years, these natural products have become a test bed for new methods for the construction of THP rings.

KW - tetrahydropyran

KW - total synthesis

KW - natural products

KW - MAITLAND-JAPP REACTION

KW - TRANSANNULAR CONJUGATE ADDITION

KW - PHORBOXAZOLE-B

KW - PRINS CYCLIZATION

KW - APICULAREN-A

KW - STEREOSELECTIVE-SYNTHESIS

KW - REGIOSELECTIVE SYNTHESIS

KW - HEXACYCLINIC ACID

KW - LASONOLIDE-A

KW - ONE-POT

U2 - 10.1002/ejoc.200500964

DO - 10.1002/ejoc.200500964

M3 - Literature review

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EP - 2053

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

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