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Open AccessCommunication
Mar. Drugs 2017, 15(1), 17; doi:10.3390/md15010017

Asymmetric Total Synthesis of Ieodomycin B

1
School of Pharmacy, Jiangxi Science and Technology Normal University, Fenglin Road 605, Nanchang 330013, China
2
School of Life Science, Jiangxi Science and Technology Normal University, Fenglin Road 605, Nanchang 330013, China
*
Authors to whom correspondence should be addressed.
Academic Editor: Vassilios Roussis
Received: 31 August 2016 / Revised: 29 November 2016 / Accepted: 8 December 2016 / Published: 18 January 2017
(This article belongs to the Special Issue Marine Fungal Natural Products)
View Full-Text   |   Download PDF [1563 KB, uploaded 18 January 2017]   |  

Abstract

Ieodomycin B, which shows in vitro antimicrobial activity, was isolated from a marine Bacillus species. A novel asymmetric total synthetic approach to ieodomycin B using commercially available geraniol was achieved. The approach involves the generation of 1,3-trans-dihydroxyl at C-3 and C-5 positions via a Crimmins-modified Evans aldol reaction and a chelation-controlled Mukaiyama aldol reaction of a p-methoxybenzyl-protected aldehyde, as well as the generation of a lactone ring in a deprotection–lactonization one-pot reaction. View Full-Text
Keywords: antimicrobial; total synthesis; ieodomycin B; chelation-controlled Mukaiyama aldol reaction antimicrobial; total synthesis; ieodomycin B; chelation-controlled Mukaiyama aldol reaction
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Lin, S.; Zhang, J.; Zhang, Z.; Xu, T.; Huang, S.; Wang, X. Asymmetric Total Synthesis of Ieodomycin B. Mar. Drugs 2017, 15, 17.

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