Total Synthesis of (+)-Lycoricidine and Conduramine B-1, ent-C-1, C-4, D-1, ent-F-1, and ent-F-4, and Formal Synthesis of (-)-Laminitol: a C2-Symmetric Chiral-Pool-Based Flexible Strategy

Hong-Jay Lo; Yuan-Kang Chang; Bakthavachalam Ananthan; Yu-Hsuan Lih; Kuang-Shun Liu; Tu-Hsin Yan

doi:10.1021/acs.joc.9b01221

Total Synthesis of (+)-Lycoricidine and Conduramine B-1, ent-C-1, C-4, D-1, ent-F-1, and ent-F-4, and Formal Synthesis of (-)-Laminitol: a C₂-Symmetric Chiral-Pool-Based Flexible Strategy

J Org Chem. 2019 Aug 16;84(16):10065-10075. doi: 10.1021/acs.joc.9b01221. Epub 2019 Aug 5.

Authors

Hong-Jay Lo¹, Yuan-Kang Chang¹, Bakthavachalam Ananthan¹, Yu-Hsuan Lih¹, Kuang-Shun Liu¹, Tu-Hsin Yan¹

Affiliation

¹ Department of Chemistry , National Chung Hsing University , Taichung 402 , Taiwan.

PMID: 31331167
DOI: 10.1021/acs.joc.9b01221

Abstract

A facile and diversity-oriented synthetic strategy toward aminocyclitol natural products from inexpensive C₂-symmetric l-tartaric acid was developed. The pivotal epoxide was used as a common intermediate to accomplish eight diverse target molecules in six to eleven steps. Various allyl-amine-type conduramines were synthesized in a diastereoselective manner. Heck arylation was explored to construct a phenanthridone ring in a concise synthesis of (+)-lycoricidine. In addition, a highly efficient formal synthesis of (-)-laminitol was developed.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amaryllidaceae Alkaloids / chemical synthesis*
Amaryllidaceae Alkaloids / chemistry
Amines / chemical synthesis*
Amines / chemistry
Cyclohexenes / chemical synthesis*
Cyclohexenes / chemistry
Inositol / analogs & derivatives*
Inositol / chemical synthesis
Inositol / chemistry
Molecular Structure
Phenanthridines / chemical synthesis*
Phenanthridines / chemistry
Phenols / chemical synthesis*
Phenols / chemistry
Stereoisomerism

Substances

Amaryllidaceae Alkaloids
Amines
Cyclohexenes
Phenanthridines
Phenols
conduramine B-1
lycoricidine
laminitol
Inositol