Diastereoselective construction of cis 2,6-disubstituted tetrahydropyran rings via In(OTf)3-catalyzed intramolecular 2,5-oxonium-ene cyclization: Synthetic studies towards the total synthesis of zampanolide and dactylolide

Teck Peng Loh; Jian Ying Yang; Li Chun Feng; Yan Zhou

doi:10.1016/S0040-4039(02)01666-0

Diastereoselective construction of cis 2,6-disubstituted tetrahydropyran rings via In(OTf)₃-catalyzed intramolecular 2,5-oxonium-ene cyclization: Synthetic studies towards the total synthesis of zampanolide and dactylolide

Teck Peng Loh^*, Jian Ying Yang, Li Chun Feng, Yan Zhou

^*Corresponding author for this work

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

35 Citations (Scopus)

Abstract

Diastereoselective construction of 2,6-disubstituted tetrahydropyrans with an exocyclic double bond was achieved via the In(OTf)₃-catalyzed intramolecular 2,5-oxonium-ene cyclization. Its application was further demonstrated by the synthesis of a common intermediate for both zampanolide and dactylolide, fragment I, with a total yield of 42% in three steps starting from (2E)-3-bromobut-2-enal.

Original language	English
Pages (from-to)	7193-7196
Number of pages	4
Journal	Tetrahedron Letters
Volume	43
Issue number	40
DOIs	https://doi.org/10.1016/S0040-4039(02)01666-0
Publication status	Published - Sept 30 2002
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

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@article{0ab6d6ce014c4fee879735efaaf22ed3,

title = "Diastereoselective construction of cis 2,6-disubstituted tetrahydropyran rings via In(OTf)3-catalyzed intramolecular 2,5-oxonium-ene cyclization: Synthetic studies towards the total synthesis of zampanolide and dactylolide",

abstract = "Diastereoselective construction of 2,6-disubstituted tetrahydropyrans with an exocyclic double bond was achieved via the In(OTf)3-catalyzed intramolecular 2,5-oxonium-ene cyclization. Its application was further demonstrated by the synthesis of a common intermediate for both zampanolide and dactylolide, fragment I, with a total yield of 42% in three steps starting from (2E)-3-bromobut-2-enal.",

author = "Loh, {Teck Peng} and Yang, {Jian Ying} and Feng, {Li Chun} and Yan Zhou",

year = "2002",

month = sep,

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doi = "10.1016/S0040-4039(02)01666-0",

language = "English",

volume = "43",

pages = "7193--7196",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "40",

}

Diastereoselective construction of cis 2,6-disubstituted tetrahydropyran rings via In(OTf)₃-catalyzed intramolecular 2,5-oxonium-ene cyclization: Synthetic studies towards the total synthesis of zampanolide and dactylolide. / Loh, Teck Peng; Yang, Jian Ying; Feng, Li Chun et al.
In: Tetrahedron Letters, Vol. 43, No. 40, 30.09.2002, p. 7193-7196.

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

TY - JOUR

T1 - Diastereoselective construction of cis 2,6-disubstituted tetrahydropyran rings via In(OTf)3-catalyzed intramolecular 2,5-oxonium-ene cyclization

T2 - Synthetic studies towards the total synthesis of zampanolide and dactylolide

AU - Loh, Teck Peng

AU - Yang, Jian Ying

AU - Feng, Li Chun

AU - Zhou, Yan

PY - 2002/9/30

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AB - Diastereoselective construction of 2,6-disubstituted tetrahydropyrans with an exocyclic double bond was achieved via the In(OTf)3-catalyzed intramolecular 2,5-oxonium-ene cyclization. Its application was further demonstrated by the synthesis of a common intermediate for both zampanolide and dactylolide, fragment I, with a total yield of 42% in three steps starting from (2E)-3-bromobut-2-enal.

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