Stereoselective total synthesis of (−)-galantinic acid and 1-deoxy-5-hydroxysphingolipids via prins cyclization

Md Ataur Rahman; Ashanul Haque; Jhillu Singh Yadav

doi:10.1016/j.tetlet.2020.152149

Stereoselective total synthesis of (−)-galantinic acid and 1-deoxy-5-hydroxysphingolipids via prins cyclization

Md Ataur Rahman
, Ashanul Haque
, Jhillu Singh Yadav

New York University Abu Dhabi

CSIR - Indian Institute of Chemical Technology
University of Hail

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

5 Scopus citations

Abstract

The stereoselective total synthesis of (−)-galantinic acid 1 and 1-deoxy-5-hydroxysphingolipids 4 is described via Prins cyclization protocol followed by reductive ring opening sequence of substituted pyrenol derivative 6. The target molecules were synthesized using a common synthetic intermediate epoxide 5. Besides, we also proposed synthetic pathways to achieve other structural analogues using common intermediates.

Original language	English
Article number	152149
Journal	Tetrahedron Letters
Volume	61
Issue number	30
DOIs	https://doi.org/10.1016/j.tetlet.2020.152149
State	Published - 23 Jul 2020

Keywords

Mitsunobu reaction
Natural products
Prins cyclization
Reductive ring opening sequence
Sharpless epoxidation

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10.1016/j.tetlet.2020.152149

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title = "Stereoselective total synthesis of (−)-galantinic acid and 1-deoxy-5-hydroxysphingolipids via prins cyclization",

abstract = "The stereoselective total synthesis of (−)-galantinic acid 1 and 1-deoxy-5-hydroxysphingolipids 4 is described via Prins cyclization protocol followed by reductive ring opening sequence of substituted pyrenol derivative 6. The target molecules were synthesized using a common synthetic intermediate epoxide 5. Besides, we also proposed synthetic pathways to achieve other structural analogues using common intermediates.",

keywords = "Mitsunobu reaction, Natural products, Prins cyclization, Reductive ring opening sequence, Sharpless epoxidation",

author = "Rahman, \{Md Ataur\} and Ashanul Haque and Yadav, \{Jhillu Singh\}",

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AU - Rahman, Md Ataur

AU - Haque, Ashanul

AU - Yadav, Jhillu Singh

PY - 2020/7/23

Y1 - 2020/7/23

N2 - The stereoselective total synthesis of (−)-galantinic acid 1 and 1-deoxy-5-hydroxysphingolipids 4 is described via Prins cyclization protocol followed by reductive ring opening sequence of substituted pyrenol derivative 6. The target molecules were synthesized using a common synthetic intermediate epoxide 5. Besides, we also proposed synthetic pathways to achieve other structural analogues using common intermediates.

AB - The stereoselective total synthesis of (−)-galantinic acid 1 and 1-deoxy-5-hydroxysphingolipids 4 is described via Prins cyclization protocol followed by reductive ring opening sequence of substituted pyrenol derivative 6. The target molecules were synthesized using a common synthetic intermediate epoxide 5. Besides, we also proposed synthetic pathways to achieve other structural analogues using common intermediates.

KW - Mitsunobu reaction

KW - Natural products

KW - Prins cyclization

KW - Reductive ring opening sequence

KW - Sharpless epoxidation

UR - https://www.scopus.com/pages/publications/85086935617

U2 - 10.1016/j.tetlet.2020.152149

DO - 10.1016/j.tetlet.2020.152149

M3 - Article

AN - SCOPUS:85086935617

SN - 0040-4039

VL - 61

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 30

M1 - 152149

ER -

Stereoselective total synthesis of (−)-galantinic acid and 1-deoxy-5-hydroxysphingolipids via prins cyclization

Abstract

Keywords

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