Synthesis of stereodefined z-vinyl iodides from carbohydrates as a prelude to C/D ring assembly in taxanes

Leo A. Paquette; Tzenge Lien Shih; Qingbei Zeng; John E. Hofferberth

doi:10.1016/S0040-4039(99)00546-8

Synthesis of stereodefined z-vinyl iodides from carbohydrates as a prelude to C/D ring assembly in taxanes

Leo A. Paquette^*, Tzenge Lien Shih, Qingbei Zeng, John E. Hofferberth

^*Corresponding author for this work

Ohio State University

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

7 Scopus citations

Abstract

D-Mannitol has been transformed into 10 and 14, while D-glucose has served as precursor to 20. In the latter example, key steps include stereocontrolled vinylation, oxidative fragmentation of the tetrahydrofuran- 2,3-diol, oxetane ring closure, and highly stereoselective iodoolefination.

Original language	English
Pages (from-to)	3519-3522
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	18
DOIs	https://doi.org/10.1016/S0040-4039(99)00546-8
State	Published - 30 04 1999
Externally published	Yes

Keywords

Alkenyl halides
Carbohydrates
Oxetanes
Wittig reactions

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10.1016/S0040-4039(99)00546-8

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abstract = "D-Mannitol has been transformed into 10 and 14, while D-glucose has served as precursor to 20. In the latter example, key steps include stereocontrolled vinylation, oxidative fragmentation of the tetrahydrofuran- 2,3-diol, oxetane ring closure, and highly stereoselective iodoolefination.",

keywords = "Alkenyl halides, Carbohydrates, Oxetanes, Wittig reactions",

author = "Paquette, {Leo A.} and Shih, {Tzenge Lien} and Qingbei Zeng and Hofferberth, {John E.}",

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T1 - Synthesis of stereodefined z-vinyl iodides from carbohydrates as a prelude to C/D ring assembly in taxanes

AU - Paquette, Leo A.

AU - Shih, Tzenge Lien

AU - Zeng, Qingbei

AU - Hofferberth, John E.

PY - 1999/4/30

Y1 - 1999/4/30

N2 - D-Mannitol has been transformed into 10 and 14, while D-glucose has served as precursor to 20. In the latter example, key steps include stereocontrolled vinylation, oxidative fragmentation of the tetrahydrofuran- 2,3-diol, oxetane ring closure, and highly stereoselective iodoolefination.

AB - D-Mannitol has been transformed into 10 and 14, while D-glucose has served as precursor to 20. In the latter example, key steps include stereocontrolled vinylation, oxidative fragmentation of the tetrahydrofuran- 2,3-diol, oxetane ring closure, and highly stereoselective iodoolefination.

KW - Alkenyl halides

KW - Carbohydrates

KW - Oxetanes

KW - Wittig reactions

UR - http://www.scopus.com/inward/record.url?scp=0033617268&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(99)00546-8

DO - 10.1016/S0040-4039(99)00546-8

M3 - 文章

AN - SCOPUS:0033617268

SN - 0040-4039

VL - 40

SP - 3519

EP - 3522

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 18

ER -

Synthesis of stereodefined z-vinyl iodides from carbohydrates as a prelude to C/D ring assembly in taxanes

Abstract

Keywords

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