A divergent enantioselective synthesis of 9-J1-phytoprostane and 9-A1-phytoprostane methyl ester

Alessio Porta; Francesco Chiesa; Marco Quaroni; Marco Persico; Remigio Moratti; Giuseppe Zanoni; Giovanni Vidari

doi:10.1002/ejoc.201301703

A divergent enantioselective synthesis of 9-J1-phytoprostane and 9-A1-phytoprostane methyl ester

Alessio Porta, Francesco Chiesa, Marco Quaroni, Marco Persico, Remigio Moratti, Giuseppe Zanoni, Giovanni Vidari

IRCCS Fondazione Policlinico San Matteo

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

Abstract

The first syntheses of 9-J₁-phytoprostane and 9-A ₁-phytoprostane methyl ester were achieved enantioselectively using a divergent approach from a common intermediate sulfone 4. The divergence was accomplished using a sigmatropic rearrangement (swap protocol) to give sulfone 5 in 47% overall yield. The two upper side-chains, with a stereodefined E double bond, were installed using consolidated Julia-Lythgoe olefination reactions of sulfones 4 and 5, with the same enantiopure α-protected aldehyde 6.

Original language	English
Pages (from-to)	2111-2119
Number of pages	9
Journal	European Journal of Organic Chemistry
Volume	2014
Issue number	10
DOIs	https://doi.org/10.1002/ejoc.201301703
Publication status	Published - 2014

Keywords

Asymmetric synthesis
Natural products
Olefination
Phytoprostanes
Total synthesis

ASJC Scopus subject areas

Organic Chemistry
Physical and Theoretical Chemistry

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10.1002/ejoc.201301703

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A divergent enantioselective synthesis of 9-J1-phytoprostane and 9-A1-phytoprostane methyl ester. / Porta, Alessio; Chiesa, Francesco; Quaroni, Marco; Persico, Marco; Moratti, Remigio; Zanoni, Giuseppe; Vidari, Giovanni.

In: European Journal of Organic Chemistry, Vol. 2014, No. 10, 2014, p. 2111-2119.

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

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abstract = "The first syntheses of 9-J1-phytoprostane and 9-A 1-phytoprostane methyl ester were achieved enantioselectively using a divergent approach from a common intermediate sulfone 4. The divergence was accomplished using a sigmatropic rearrangement (swap protocol) to give sulfone 5 in 47% overall yield. The two upper side-chains, with a stereodefined E double bond, were installed using consolidated Julia-Lythgoe olefination reactions of sulfones 4 and 5, with the same enantiopure α-protected aldehyde 6.",

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AU - Persico, Marco

AU - Moratti, Remigio

AU - Zanoni, Giuseppe

AU - Vidari, Giovanni

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KW - Olefination

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KW - Total synthesis

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A divergent enantioselective synthesis of 9-J1-phytoprostane and 9-A1-phytoprostane methyl ester

Abstract

Keywords

ASJC Scopus subject areas

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