Intramolecular aldol condensation applied to d-glucose-derived δ-ketoaldehydes: access to enantiomerically pure six-membered carbocycles

Kin ichi Tadano; Satoshi Kanazawa; Ken ichi Takao; Seiichiro Ogawa

doi:10.1016/S0040-4020(01)80440-3

Intramolecular aldol condensation applied to d-glucose-derived δ-ketoaldehydes: access to enantiomerically pure six-membered carbocycles

Kin ichi Tadano
, Satoshi Kanazawa
, Ken ichi Takao
, Seiichiro Ogawa

Department of Applied Chemistry

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

8 Citations (Scopus)

Abstract

An enantiomerically pure δ-ketoaldehyde 10, efficiently prepared from D-glucose, was subjected to an intramolecular aldol condensation. By using DBU as a base, the expecting aldol reaction took place smoothly giving the aldol 11 stereoselectively. Further functionalization of 11 provided tri-C-substituted cyclohexanediols 26 and 27, via the functionalized cyclohexenone15.

Original language	English
Pages (from-to)	4283-4300
Number of pages	18
Journal	Tetrahedron
Volume	48
Issue number	21
DOIs	https://doi.org/10.1016/S0040-4020(01)80440-3
Publication status	Published - 1992

Keywords

D-glucose-derived δ-ketoaldehyde
intramolecular aldol condensation
tri-C-alkylated cyclohexanoids

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(01)80440-3

Cite this

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abstract = "An enantiomerically pure δ-ketoaldehyde 10, efficiently prepared from D-glucose, was subjected to an intramolecular aldol condensation. By using DBU as a base, the expecting aldol reaction took place smoothly giving the aldol 11 stereoselectively. Further functionalization of 11 provided tri-C-substituted cyclohexanediols 26 and 27, via the functionalized cyclohexenone15.",

keywords = "D-glucose-derived δ-ketoaldehyde, intramolecular aldol condensation, tri-C-alkylated cyclohexanoids",

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doi = "10.1016/S0040-4020(01)80440-3",

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T1 - Intramolecular aldol condensation applied to d-glucose-derived δ-ketoaldehydes

T2 - access to enantiomerically pure six-membered carbocycles

AU - Tadano, Kin ichi

AU - Kanazawa, Satoshi

AU - Takao, Ken ichi

AU - Ogawa, Seiichiro

PY - 1992

Y1 - 1992

N2 - An enantiomerically pure δ-ketoaldehyde 10, efficiently prepared from D-glucose, was subjected to an intramolecular aldol condensation. By using DBU as a base, the expecting aldol reaction took place smoothly giving the aldol 11 stereoselectively. Further functionalization of 11 provided tri-C-substituted cyclohexanediols 26 and 27, via the functionalized cyclohexenone15.

AB - An enantiomerically pure δ-ketoaldehyde 10, efficiently prepared from D-glucose, was subjected to an intramolecular aldol condensation. By using DBU as a base, the expecting aldol reaction took place smoothly giving the aldol 11 stereoselectively. Further functionalization of 11 provided tri-C-substituted cyclohexanediols 26 and 27, via the functionalized cyclohexenone15.

KW - D-glucose-derived δ-ketoaldehyde

KW - intramolecular aldol condensation

KW - tri-C-alkylated cyclohexanoids

UR - https://www.scopus.com/pages/publications/0026697107

UR - https://www.scopus.com/pages/publications/0026697107#tab=citedBy

U2 - 10.1016/S0040-4020(01)80440-3

DO - 10.1016/S0040-4020(01)80440-3

M3 - Article

AN - SCOPUS:0026697107

SN - 0040-4020

VL - 48

SP - 4283

EP - 4300

JO - Tetrahedron

JF - Tetrahedron

IS - 21

ER -

Intramolecular aldol condensation applied to d-glucose-derived δ-ketoaldehydes: access to enantiomerically pure six-membered carbocycles

Abstract

Keywords

ASJC Scopus subject areas

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