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Total synthesis of auripyrone B using a non-aldol aldol-cuprate opening process.

ABSTRACT: A non-aldol aldol-cuprate opening generates the polypropionate 11 from the epoxy ether 14 in eight steps as a single diastereomer. A highly stereoselective aldol reaction of 8 with 9 gives the aldol product 7 in high yield and excellent diastereoselectivity, due to double stereodifferentiation. This compound was used for an efficient synthesis of the natural product auripyrone B 2 in only 20 steps and 8% overall yield from 14 using a late-stage spiroketalization onto a stable hemiketal as the final key step.

SUBMITTER: Jung ME

PROVIDER: S-EPMC4099051 | biostudies-literature | 2010 Jun

REPOSITORIES: biostudies-literature

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Total synthesis of auripyrone B using a non-aldol aldol-cuprate opening process.

Jung Michael E ME Chaumontet Manon M Salehi-Rad Ramin R

Organic letters 20100601 12

A non-aldol aldol-cuprate opening generates the polypropionate 11 from the epoxy ether 14 in eight steps as a single diastereomer. A highly stereoselective aldol reaction of 8 with 9 gives the aldol product 7 in high yield and excellent diastereoselectivity, due to double stereodifferentiation. This compound was used for an efficient synthesis of the natural product auripyrone B 2 in only 20 steps and 8% overall yield from 14 using a late-stage spiroketalization onto a stable hemiketal as the fi ...[more]

PMID: 20499854

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