Development of Organoiron Methodology for Preparation of the Polyene Natural Product Macrolactin A

Authors

Heiko Bärmann
Vadapalli PrahladFollow
Chunlin Tao, Marquette University
Young K. YunFollow
Zhi Wang
William Donaldson, Marquette UniversityFollow

Document Type

Article

Publication Date

4-2000

Publisher

Elsevier

Source Publication

Tetrahedron

Source ISSN

0040-4020

Abstract

Methodology for the synthesis of the C7–C13 segment (19) and C14–C24 segment (41) of macrolactin A have been developed. Dicarbonyl(methyl 7-nitro-2E,4Z-heptadienoate)triphenylphosphineiron (19) is prepared by nucleophilic addition to a (1-methoxycarbonylpentadienyl)iron cation. The C23 stereocenter of 41 is established by introduction of a C20 stereocenter, chirality transfer from C20 to C23 followed by (diene)iron mediated selective ionic reduction of the C20 hydroxyl. The C15 stereocenter may be established by nitrile oxide–olefin cyclocondensation.

Comments

Accepted version. Tetrahedron, Vol. 56, Issue 15 (2000), pp 2283-2295. DOI: 10.1016/S0040-4020(99)01111-4. © 2000 Elsevier. Used with permission.

Recommended Citation

Bärmann, Heiko; Prahlad, Vadapalli; Tao, Chunlin; Yun, Young K.; Wang, Zhi; and Donaldson, William, "Development of Organoiron Methodology for Preparation of the Polyene Natural Product Macrolactin A" (2000). Chemistry Faculty Research and Publications. 77.
https://epublications.marquette.edu/chem_fac/77