A synthesis of pseudoconhydrine and its epimer via hydroformylation and dihydroxylation

Roderick W. Bates; K. Sivarajan; Bernd F. Straub

doi:10.1021/jo2008912

A synthesis of pseudoconhydrine and its epimer via hydroformylation and dihydroxylation

Roderick W. Bates^*, K. Sivarajan, Bernd F. Straub

^*Corresponding author for this work

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

36 Citations (Scopus)

Abstract

A synthesis of the alkaloid pseudoconhydrine and its epimer has been achieved using tandem hydroformylation-condensation to form the six-membered ring and stereoselective dihydroxylation to introduce oxygenation. The stereoselectivity of dihydroxylation can be explained by lipophilic and electrostatic effects, supported by DFT calculations. The alkaloids can be obtained either by regioselective dehydroxylation or by rearrangement, followed by reduction.

Original language	English
Pages (from-to)	6844-6848
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	76
Issue number	16
DOIs	https://doi.org/10.1021/jo2008912
Publication status	Published - Aug 19 2011
Externally published	Yes

ASJC Scopus Subject Areas

Organic Chemistry

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abstract = "A synthesis of the alkaloid pseudoconhydrine and its epimer has been achieved using tandem hydroformylation-condensation to form the six-membered ring and stereoselective dihydroxylation to introduce oxygenation. The stereoselectivity of dihydroxylation can be explained by lipophilic and electrostatic effects, supported by DFT calculations. The alkaloids can be obtained either by regioselective dehydroxylation or by rearrangement, followed by reduction.",

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AU - Straub, Bernd F.

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AB - A synthesis of the alkaloid pseudoconhydrine and its epimer has been achieved using tandem hydroformylation-condensation to form the six-membered ring and stereoselective dihydroxylation to introduce oxygenation. The stereoselectivity of dihydroxylation can be explained by lipophilic and electrostatic effects, supported by DFT calculations. The alkaloids can be obtained either by regioselective dehydroxylation or by rearrangement, followed by reduction.

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A synthesis of pseudoconhydrine and its epimer via hydroformylation and dihydroxylation

Abstract

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