Total synthesis of peloruside a through kinetic lactonization and relay ring-closing metathesis cyclization reactions

Thomas R. Hoye; Junha Jeon; Lucas C. Kopel; Troy D. Ryba; Manomi A. Tennakoon; Yini Wang

doi:10.1002/anie.201002293

Total synthesis of peloruside a through kinetic lactonization and relay ring-closing metathesis cyclization reactions

Thomas R. Hoye, Junha Jeon, Lucas C. Kopel, Troy D. Ryba, Manomi A. Tennakoon, Yini Wang

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

47 Scopus citations

Abstract

The other side: A convergent total synthesis of peloruside A (1) is described. The key strategic features are a diastereoselective lactonization to generate a C5-C9 valerolactone from the C2-symmetric ketone 3, and a relay ring-closing metathesis reaction to produce a dehydrovalerolactone 2. A new isomer of 1, the valerolactone isopeloruside A (iso-1), was identified. MOM=methoxymethyl.

Original language	English (US)
Pages (from-to)	6151-6155
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	49
Issue number	35
DOIs	https://doi.org/10.1002/anie.201002293
State	Published - Aug 16 2010

Keywords

Aldol reaction
Lactones
Metathesis
Natural products
Total synthesis

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/anie.201002293

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title = "Total synthesis of peloruside a through kinetic lactonization and relay ring-closing metathesis cyclization reactions",

abstract = "The other side: A convergent total synthesis of peloruside A (1) is described. The key strategic features are a diastereoselective lactonization to generate a C5-C9 valerolactone from the C2-symmetric ketone 3, and a relay ring-closing metathesis reaction to produce a dehydrovalerolactone 2. A new isomer of 1, the valerolactone isopeloruside A (iso-1), was identified. MOM=methoxymethyl.",

keywords = "Aldol reaction, Lactones, Metathesis, Natural products, Total synthesis",

author = "Hoye, {Thomas R.} and Junha Jeon and Kopel, {Lucas C.} and Ryba, {Troy D.} and Tennakoon, {Manomi A.} and Yini Wang",

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language = "English (US)",

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T1 - Total synthesis of peloruside a through kinetic lactonization and relay ring-closing metathesis cyclization reactions

AU - Hoye, Thomas R.

AU - Jeon, Junha

AU - Kopel, Lucas C.

AU - Ryba, Troy D.

AU - Tennakoon, Manomi A.

AU - Wang, Yini

PY - 2010/8/16

Y1 - 2010/8/16

N2 - The other side: A convergent total synthesis of peloruside A (1) is described. The key strategic features are a diastereoselective lactonization to generate a C5-C9 valerolactone from the C2-symmetric ketone 3, and a relay ring-closing metathesis reaction to produce a dehydrovalerolactone 2. A new isomer of 1, the valerolactone isopeloruside A (iso-1), was identified. MOM=methoxymethyl.

AB - The other side: A convergent total synthesis of peloruside A (1) is described. The key strategic features are a diastereoselective lactonization to generate a C5-C9 valerolactone from the C2-symmetric ketone 3, and a relay ring-closing metathesis reaction to produce a dehydrovalerolactone 2. A new isomer of 1, the valerolactone isopeloruside A (iso-1), was identified. MOM=methoxymethyl.

KW - Aldol reaction

KW - Lactones

KW - Metathesis

KW - Natural products

KW - Total synthesis

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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Total synthesis of peloruside a through kinetic lactonization and relay ring-closing metathesis cyclization reactions

Abstract

Keywords

UN SDGs

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