Concise syntheses of (+)-macrosphelides A and B

Seung Mann Paek; Seung Yong Seo; Seok Ho Kim; Jong Wha Jung; Yong Sil Lee; Jae Kyung Jung; Young Ger Suh

doi:10.1021/ol0508429

Concise syntheses of (+)-macrosphelides A and B

Seung Mann Paek, Seung Yong Seo, Seok Ho Kim, Jong Wha Jung, Yong Sil Lee, Jae Kyung Jung, Young Ger Suh

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Abstract

(Chemical Equation Presented) Unified and highly convergent total syntheses of (+)-macrosphelides A and B are described. Key features of the syntheses include (1) concise synthesis of the optically active δ-hydroxy-γ- keto α,β-unsaturated acid fragment via the direct addition of a trans-vinylogous ester anion equivalent to the readily available Weinreb amide and (2) facile construction of the 16-membered macrolide core of the macrosphelide series via an intramolecular nitrile-oxide cycloaddition (INOC).

Original language	English
Pages (from-to)	3159-3162
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	15
DOIs	https://doi.org/10.1021/ol0508429
State	Published - 21 Jul 2005

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title = "Concise syntheses of (+)-macrosphelides A and B",

abstract = "(Chemical Equation Presented) Unified and highly convergent total syntheses of (+)-macrosphelides A and B are described. Key features of the syntheses include (1) concise synthesis of the optically active δ-hydroxy-γ- keto α,β-unsaturated acid fragment via the direct addition of a trans-vinylogous ester anion equivalent to the readily available Weinreb amide and (2) facile construction of the 16-membered macrolide core of the macrosphelide series via an intramolecular nitrile-oxide cycloaddition (INOC).",

author = "Paek, {Seung Mann} and Seo, {Seung Yong} and Kim, {Seok Ho} and Jung, {Jong Wha} and Lee, {Yong Sil} and Jung, {Jae Kyung} and Suh, {Young Ger}",

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doi = "10.1021/ol0508429",

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T1 - Concise syntheses of (+)-macrosphelides A and B

AU - Paek, Seung Mann

AU - Seo, Seung Yong

AU - Kim, Seok Ho

AU - Jung, Jong Wha

AU - Lee, Yong Sil

AU - Jung, Jae Kyung

AU - Suh, Young Ger

PY - 2005/7/21

Y1 - 2005/7/21

N2 - (Chemical Equation Presented) Unified and highly convergent total syntheses of (+)-macrosphelides A and B are described. Key features of the syntheses include (1) concise synthesis of the optically active δ-hydroxy-γ- keto α,β-unsaturated acid fragment via the direct addition of a trans-vinylogous ester anion equivalent to the readily available Weinreb amide and (2) facile construction of the 16-membered macrolide core of the macrosphelide series via an intramolecular nitrile-oxide cycloaddition (INOC).

AB - (Chemical Equation Presented) Unified and highly convergent total syntheses of (+)-macrosphelides A and B are described. Key features of the syntheses include (1) concise synthesis of the optically active δ-hydroxy-γ- keto α,β-unsaturated acid fragment via the direct addition of a trans-vinylogous ester anion equivalent to the readily available Weinreb amide and (2) facile construction of the 16-membered macrolide core of the macrosphelide series via an intramolecular nitrile-oxide cycloaddition (INOC).

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U2 - 10.1021/ol0508429

DO - 10.1021/ol0508429

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VL - 7

SP - 3159

EP - 3162

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Concise syntheses of (+)-macrosphelides A and B

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