Stereoselective Synthesis of the C27-C48 Moiety of Aflastatin A by a Carbohydrate Strategy Using a Tin(II)-Mediated Aldol Reaction

Sawato Murakoshi; Seijiro Hosokawa

doi:10.1055/s-0035-1560572

Stereoselective Synthesis of the C27-C48 Moiety of Aflastatin A by a Carbohydrate Strategy Using a Tin(II)-Mediated Aldol Reaction

Sawato Murakoshi, Seijiro Hosokawa^*

^*Corresponding author for this work

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

6 Citations (Scopus)

Abstract

The C27-C48 segment of aflastatin A was synthesized by using d-mannoside and l-erythrulose derivatives as chiral building blocks. The aldol reaction of undecan-2-one with mannolactone and a subsequent reduction gave the C37 and C39 stereogenic centers with high selectivity. Another aldol reaction of a tin(II) enolate of a protected erythrulose (C27-C30 segment) with a C31-C48 aldehyde segment gave the C30,C31-syn adduct with the desired stereochemistry. Deprotection of the assembled product proceeded smoothly to give the C27-C48 segment of aflastatin A containing a contiguous polyol moiety.

Original language	English
Article number	st-2015-u0570-l
Pages (from-to)	2437-2441
Number of pages	5
Journal	Synlett
Volume	26
Issue number	17
DOIs	https://doi.org/10.1055/s-0035-1560572
Publication status	Published - 2015 Oct 22

Keywords

aflastatin A
aldol reactions
carbohydrates
polyols
stereoselectivity

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-0035-1560572

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abstract = "The C27-C48 segment of aflastatin A was synthesized by using d-mannoside and l-erythrulose derivatives as chiral building blocks. The aldol reaction of undecan-2-one with mannolactone and a subsequent reduction gave the C37 and C39 stereogenic centers with high selectivity. Another aldol reaction of a tin(II) enolate of a protected erythrulose (C27-C30 segment) with a C31-C48 aldehyde segment gave the C30,C31-syn adduct with the desired stereochemistry. Deprotection of the assembled product proceeded smoothly to give the C27-C48 segment of aflastatin A containing a contiguous polyol moiety.",

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AU - Murakoshi, Sawato

AU - Hosokawa, Seijiro

PY - 2015/10/22

Y1 - 2015/10/22

N2 - The C27-C48 segment of aflastatin A was synthesized by using d-mannoside and l-erythrulose derivatives as chiral building blocks. The aldol reaction of undecan-2-one with mannolactone and a subsequent reduction gave the C37 and C39 stereogenic centers with high selectivity. Another aldol reaction of a tin(II) enolate of a protected erythrulose (C27-C30 segment) with a C31-C48 aldehyde segment gave the C30,C31-syn adduct with the desired stereochemistry. Deprotection of the assembled product proceeded smoothly to give the C27-C48 segment of aflastatin A containing a contiguous polyol moiety.

AB - The C27-C48 segment of aflastatin A was synthesized by using d-mannoside and l-erythrulose derivatives as chiral building blocks. The aldol reaction of undecan-2-one with mannolactone and a subsequent reduction gave the C37 and C39 stereogenic centers with high selectivity. Another aldol reaction of a tin(II) enolate of a protected erythrulose (C27-C30 segment) with a C31-C48 aldehyde segment gave the C30,C31-syn adduct with the desired stereochemistry. Deprotection of the assembled product proceeded smoothly to give the C27-C48 segment of aflastatin A containing a contiguous polyol moiety.

KW - aflastatin A

KW - aldol reactions

KW - carbohydrates

KW - polyols

KW - stereoselectivity

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Stereoselective Synthesis of the C27-C48 Moiety of Aflastatin A by a Carbohydrate Strategy Using a Tin(II)-Mediated Aldol Reaction

Abstract

Keywords

ASJC Scopus subject areas

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