Further studies of an approach to a total synthesis of phomactins

Timothy J. Blackburn; Madeleine Helliwell; Michael J. Kilner; Alan T L Lee; Eric J. Thomas

doi:10.1016/j.tetlet.2009.03.042

Further studies of an approach to a total synthesis of phomactins

Timothy J. Blackburn, Madeleine Helliwell, Michael J. Kilner, Alan T L Lee, Eric J. Thomas

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

Abstract

The bicyclic sulfone 28, which has the intact carbon skeleton of phomactins, was prepared using a stereoselective [2,3]-Wittig Still rearrangement, a ytterbium triflate-mediated addition of a vinyllithium reagent to an aldehyde and macrocyclisation via an intramolecular sulfone alkylation, as key steps. During studies into the conversion of this intermediate into phomactin A, it was found that oxidation of homoallylic alcohols using TPAP can give unsaturated keto-aldehydes, and the stereoselectivity of reduction of a ketone at C(14) is influenced by the presence of a remote sulfonyl group at C(10). © 2009 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	3550-3554
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	26
DOIs	https://doi.org/10.1016/j.tetlet.2009.03.042
Publication status	Published - 1 Jul 2009

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10.1016/j.tetlet.2009.03.042

CCDC 712105: Experimental Crystal Structure Determination
Blackburn, T. J. (Contributor), Helliwell, M. (Contributor), Kilner, M. J. (Contributor), Lee, A. T. L. (Contributor) & Thomas, E. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2010
DOI: 10.5517/ccrx04s, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccrx04s&sid=DataCite
Dataset
CCDC 712103: Experimental Crystal Structure Determination
Blackburn, T. (Creator), Helliwell, M. (Creator), Kilner, M. (Creator), Lee, A. T. L. (Creator) & Thomas, E. (Creator), Cambridge Crystallographic Data Centre, 4 Dec 2008
DOI: 10.5517/ccrx02q
Dataset
CCDC 712104: Experimental Crystal Structure Determination
Blackburn, T. J. (Contributor), Helliwell, M. (Contributor), Kilner, M. J. (Contributor), Lee, A. T. L. (Contributor) & Thomas, E. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2010
DOI: 10.5517/ccrx03r, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccrx03r&sid=DataCite
Dataset

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title = "Further studies of an approach to a total synthesis of phomactins",

abstract = "The bicyclic sulfone 28, which has the intact carbon skeleton of phomactins, was prepared using a stereoselective [2,3]-Wittig Still rearrangement, a ytterbium triflate-mediated addition of a vinyllithium reagent to an aldehyde and macrocyclisation via an intramolecular sulfone alkylation, as key steps. During studies into the conversion of this intermediate into phomactin A, it was found that oxidation of homoallylic alcohols using TPAP can give unsaturated keto-aldehydes, and the stereoselectivity of reduction of a ketone at C(14) is influenced by the presence of a remote sulfonyl group at C(10). {\textcopyright} 2009 Elsevier Ltd. All rights reserved.",

author = "Blackburn, {Timothy J.} and Madeleine Helliwell and Kilner, {Michael J.} and Lee, {Alan T L} and Thomas, {Eric J.}",

year = "2009",

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doi = "10.1016/j.tetlet.2009.03.042",

language = "English",

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pages = "3550--3554",

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T1 - Further studies of an approach to a total synthesis of phomactins

AU - Blackburn, Timothy J.

AU - Helliwell, Madeleine

AU - Kilner, Michael J.

AU - Lee, Alan T L

AU - Thomas, Eric J.

PY - 2009/7/1

Y1 - 2009/7/1

N2 - The bicyclic sulfone 28, which has the intact carbon skeleton of phomactins, was prepared using a stereoselective [2,3]-Wittig Still rearrangement, a ytterbium triflate-mediated addition of a vinyllithium reagent to an aldehyde and macrocyclisation via an intramolecular sulfone alkylation, as key steps. During studies into the conversion of this intermediate into phomactin A, it was found that oxidation of homoallylic alcohols using TPAP can give unsaturated keto-aldehydes, and the stereoselectivity of reduction of a ketone at C(14) is influenced by the presence of a remote sulfonyl group at C(10). © 2009 Elsevier Ltd. All rights reserved.

AB - The bicyclic sulfone 28, which has the intact carbon skeleton of phomactins, was prepared using a stereoselective [2,3]-Wittig Still rearrangement, a ytterbium triflate-mediated addition of a vinyllithium reagent to an aldehyde and macrocyclisation via an intramolecular sulfone alkylation, as key steps. During studies into the conversion of this intermediate into phomactin A, it was found that oxidation of homoallylic alcohols using TPAP can give unsaturated keto-aldehydes, and the stereoselectivity of reduction of a ketone at C(14) is influenced by the presence of a remote sulfonyl group at C(10). © 2009 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.tetlet.2009.03.042

DO - 10.1016/j.tetlet.2009.03.042

M3 - Article

VL - 50

SP - 3550

EP - 3554

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 26

ER -

Further studies of an approach to a total synthesis of phomactins

Abstract

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Datasets

CCDC 712105: Experimental Crystal Structure Determination

CCDC 712103: Experimental Crystal Structure Determination

CCDC 712104: Experimental Crystal Structure Determination

Cite this