Total synthesis of (+)-concanamycin F

Ian Paterson; Victoria A. Doughty; Malcolm D. McLeod; Thomas Trieselmann

doi:10.1002/(SICI)1521-3773(20000403)39:7<1308::AID-ANIE1308>3.0.CO;2-7

Total synthesis of (+)-concanamycin F

Ian Paterson^*, Victoria A. Doughty, Malcolm D. McLeod, Thomas Trieselmann

^*Corresponding author for this work

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

45 Citations (Scopus)

Abstract

The choice of protecting groups proved imperative for successful macrocyclization in the total synthesis of the 18-membered macrolide concanamycin F (1), which is a potent inhibitor of vacuolar (H⁺) ATPases. A C₁₄-C₂₂ subunit was prepared with complete stereocontrol by using asymmetric, boron-mediated, aldol reactions with appropriate chiral ketones. Other key steps included a copper(I)-mediated, Liebeskind cross-coupling and a Mukaiyama aldol reaction for subunit assembly.

Original language	English
Pages (from-to)	1308-1312
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	39
Issue number	7
DOIs	https://doi.org/10.1002/(SICI)1521-3773(20000403)39:7<1308::AID-ANIE1308>3.0.CO;2-7
Publication status	Published - 3 Apr 2000
Externally published	Yes

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10.1002/(SICI)1521-3773(20000403)39:7<1308::AID-ANIE1308>3.0.CO;2-7

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title = "Total synthesis of (+)-concanamycin F",

abstract = "The choice of protecting groups proved imperative for successful macrocyclization in the total synthesis of the 18-membered macrolide concanamycin F (1), which is a potent inhibitor of vacuolar (H+) ATPases. A C14-C22 subunit was prepared with complete stereocontrol by using asymmetric, boron-mediated, aldol reactions with appropriate chiral ketones. Other key steps included a copper(I)-mediated, Liebeskind cross-coupling and a Mukaiyama aldol reaction for subunit assembly.",

keywords = "Aldol reactions, Boron, Macrolides, Natural products, Total synthesis",

author = "Ian Paterson and Doughty, {Victoria A.} and McLeod, {Malcolm D.} and Thomas Trieselmann",

year = "2000",

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doi = "10.1002/(SICI)1521-3773(20000403)39:7<1308::AID-ANIE1308>3.0.CO;2-7",

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T1 - Total synthesis of (+)-concanamycin F

AU - Paterson, Ian

AU - Doughty, Victoria A.

AU - McLeod, Malcolm D.

AU - Trieselmann, Thomas

PY - 2000/4/3

Y1 - 2000/4/3

N2 - The choice of protecting groups proved imperative for successful macrocyclization in the total synthesis of the 18-membered macrolide concanamycin F (1), which is a potent inhibitor of vacuolar (H+) ATPases. A C14-C22 subunit was prepared with complete stereocontrol by using asymmetric, boron-mediated, aldol reactions with appropriate chiral ketones. Other key steps included a copper(I)-mediated, Liebeskind cross-coupling and a Mukaiyama aldol reaction for subunit assembly.

AB - The choice of protecting groups proved imperative for successful macrocyclization in the total synthesis of the 18-membered macrolide concanamycin F (1), which is a potent inhibitor of vacuolar (H+) ATPases. A C14-C22 subunit was prepared with complete stereocontrol by using asymmetric, boron-mediated, aldol reactions with appropriate chiral ketones. Other key steps included a copper(I)-mediated, Liebeskind cross-coupling and a Mukaiyama aldol reaction for subunit assembly.

KW - Aldol reactions

KW - Boron

KW - Macrolides

KW - Natural products

KW - Total synthesis

UR - http://www.scopus.com/inward/record.url?scp=0034599684&partnerID=8YFLogxK

U2 - 10.1002/(SICI)1521-3773(20000403)39:7<1308::AID-ANIE1308>3.0.CO;2-7

DO - 10.1002/(SICI)1521-3773(20000403)39:7<1308::AID-ANIE1308>3.0.CO;2-7

M3 - Article

SN - 1433-7851

VL - 39

SP - 1308

EP - 1312

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 7

ER -

Total synthesis of (+)-concanamycin F

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