Asymmetric Total Synthesis of Ieodomycin B

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 position...

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Main Authors:	Shuangjie Lin, Jianting Zhang, Zhibin Zhang, Tianxiang Xu, Shuangping Huang, Xiaoji Wang
Format:	Article
Language:	English
Published:	MDPI AG 2017-01-01
Series:	Marine Drugs
Subjects:	antimicrobial total synthesis ieodomycin B chelation-controlled Mukaiyama aldol reaction
Online Access:	http://www.mdpi.com/1660-3397/15/1/17

id	doaj-c5ef6101c09a43588b86df5603231c09
record_format	Article
spelling	doaj-c5ef6101c09a43588b86df5603231c092020-11-24T20:48:55ZengMDPI AGMarine Drugs1660-33972017-01-011511710.3390/md15010017md15010017Asymmetric Total Synthesis of Ieodomycin BShuangjie Lin0Jianting Zhang1Zhibin Zhang2Tianxiang Xu3Shuangping Huang4Xiaoji Wang5School of Pharmacy, Jiangxi Science and Technology Normal University, Fenglin Road 605, Nanchang 330013, ChinaSchool of Pharmacy, Jiangxi Science and Technology Normal University, Fenglin Road 605, Nanchang 330013, ChinaSchool of Pharmacy, Jiangxi Science and Technology Normal University, Fenglin Road 605, Nanchang 330013, ChinaSchool of Pharmacy, Jiangxi Science and Technology Normal University, Fenglin Road 605, Nanchang 330013, ChinaSchool of Pharmacy, Jiangxi Science and Technology Normal University, Fenglin Road 605, Nanchang 330013, ChinaSchool of Life Science, Jiangxi Science and Technology Normal University, Fenglin Road 605, Nanchang 330013, ChinaIeodomycin 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.http://www.mdpi.com/1660-3397/15/1/17antimicrobialtotal synthesisieodomycin Bchelation-controlled Mukaiyama aldol reaction
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Shuangjie Lin Jianting Zhang Zhibin Zhang Tianxiang Xu Shuangping Huang Xiaoji Wang
spellingShingle	Shuangjie Lin Jianting Zhang Zhibin Zhang Tianxiang Xu Shuangping Huang Xiaoji Wang Asymmetric Total Synthesis of Ieodomycin B Marine Drugs antimicrobial total synthesis ieodomycin B chelation-controlled Mukaiyama aldol reaction
author_facet	Shuangjie Lin Jianting Zhang Zhibin Zhang Tianxiang Xu Shuangping Huang Xiaoji Wang
author_sort	Shuangjie Lin
title	Asymmetric Total Synthesis of Ieodomycin B
title_short	Asymmetric Total Synthesis of Ieodomycin B
title_full	Asymmetric Total Synthesis of Ieodomycin B
title_fullStr	Asymmetric Total Synthesis of Ieodomycin B
title_full_unstemmed	Asymmetric Total Synthesis of Ieodomycin B
title_sort	asymmetric total synthesis of ieodomycin b
publisher	MDPI AG
series	Marine Drugs
issn	1660-3397
publishDate	2017-01-01
description	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.
topic	antimicrobial total synthesis ieodomycin B chelation-controlled Mukaiyama aldol reaction
url	http://www.mdpi.com/1660-3397/15/1/17
work_keys_str_mv	AT shuangjielin asymmetrictotalsynthesisofieodomycinb AT jiantingzhang asymmetrictotalsynthesisofieodomycinb AT zhibinzhang asymmetrictotalsynthesisofieodomycinb AT tianxiangxu asymmetrictotalsynthesisofieodomycinb AT shuangpinghuang asymmetrictotalsynthesisofieodomycinb AT xiaojiwang asymmetrictotalsynthesisofieodomycinb
_version_	1716807463101005824

Asymmetric Total Synthesis of Ieodomycin B

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