Studies towards total synthesis of borrelidin, stereoselective synthesis of the polysubstituted macrolidic part

Nizar Haddad; Michael Grishko; Ashraf Brik

doi:10.1016/S0040-4039(97)01371-3

Studies towards total synthesis of borrelidin, stereoselective synthesis of the polysubstituted macrolidic part

Nizar Haddad, Michael Grishko, Ashraf Brik

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

21 Scopus citations

Abstract

Enantioselective synthesis of the polysubstituted macrolidic part of borrelidin (1) is presented. Six out of the nine stereogenic centers in 12 and 13 were achieved in >99.2 %ee in seven steps from meso-diol 4. The synthesis is based on enantioselective formation of bis-epoxide 10 followed by regioselective alkylation of the epoxide functionalities.

Original language	English
Pages (from-to)	6075-6078
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	34
DOIs	https://doi.org/10.1016/S0040-4039(97)01371-3
State	Published - 1 Aug 1997
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Studies towards total synthesis of borrelidin, stereoselective synthesis of the polysubstituted macrolidic part",

abstract = "Enantioselective synthesis of the polysubstituted macrolidic part of borrelidin (1) is presented. Six out of the nine stereogenic centers in 12 and 13 were achieved in >99.2 %ee in seven steps from meso-diol 4. The synthesis is based on enantioselective formation of bis-epoxide 10 followed by regioselective alkylation of the epoxide functionalities.",

author = "Nizar Haddad and Michael Grishko and Ashraf Brik",

note = "Funding Information: This research was supported by grant No. 95-00222 from the United States-Israel Binational Science Foundation (BSF), Jerusalem, Israel.",

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T1 - Studies towards total synthesis of borrelidin, stereoselective synthesis of the polysubstituted macrolidic part

AU - Haddad, Nizar

AU - Grishko, Michael

AU - Brik, Ashraf

N1 - Funding Information: This research was supported by grant No. 95-00222 from the United States-Israel Binational Science Foundation (BSF), Jerusalem, Israel.

PY - 1997/8/1

Y1 - 1997/8/1

N2 - Enantioselective synthesis of the polysubstituted macrolidic part of borrelidin (1) is presented. Six out of the nine stereogenic centers in 12 and 13 were achieved in >99.2 %ee in seven steps from meso-diol 4. The synthesis is based on enantioselective formation of bis-epoxide 10 followed by regioselective alkylation of the epoxide functionalities.

AB - Enantioselective synthesis of the polysubstituted macrolidic part of borrelidin (1) is presented. Six out of the nine stereogenic centers in 12 and 13 were achieved in >99.2 %ee in seven steps from meso-diol 4. The synthesis is based on enantioselective formation of bis-epoxide 10 followed by regioselective alkylation of the epoxide functionalities.

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U2 - 10.1016/S0040-4039(97)01371-3

DO - 10.1016/S0040-4039(97)01371-3

M3 - Article

AN - SCOPUS:0030737649

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JO - Tetrahedron Letters

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IS - 34

ER -

Studies towards total synthesis of borrelidin, stereoselective synthesis of the polysubstituted macrolidic part

Abstract

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