Synthesis of the C19–C30 bis-THF fragment of iriomoteolide-13a via stepwise SN2 cyclization and intramolecular syn-oxypalladation-Reference-Cited by-同舟云学术

Synthesis of the C19–C30 bis-THF fragment of iriomoteolide-13a via stepwise SN2 cyclization and intramolecular syn-oxypalladation

Published:2021 Issue:23 Volume:8 Page:6491-6498
ISSN:2052-4129
Container-title:Organic Chemistry Frontiers
language:en
Short-container-title:Org. Chem. Front.

Author:

Zhao Hui¹^ORCID,Gao Kai¹²^ORCID,Ma Haichen¹^ORCID,Yip Tsz Chun¹^ORCID,Dai Wei-Min¹^ORCID

Affiliation:

1. Hong Kong Branch of the Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou), and Laboratory of Advanced Catalysis and Synthesis, Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, P. R. China

2. School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, P. R. China

Abstract

The bis-THF subunit of iriomoteolide-13a was stereoselectively constructed from the non-protected ene triol via syn-oxypalladation with excellent atom efficiency.

Funder

Research Grants Council, University Grants Committee

Southern Marine Science and Engineering Guangdong Laboratory

Hong Kong University of Science and Technology

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2021/QO/D1QO01049B

Reference50 articles.

1. Iriomoteolide-13a, a cytotoxic 22-membered macrolide from a marine dinoflagellate Amphidinium species

2. Iriomoteolide-2a, a Cytotoxic 23-Membered Macrolide from Marine Benthic Dinoflagellate Amphidinium Species

3. Total Synthesis and Stereochemical Revision of Iriomoteolide-2a

4. Total Synthesis, Stereochemical Revision, and Biological Assessment of Iriomoteolide‐2a

5. Studies toward the Synthesis of Iriomoteolide-2a: Construction of the C(6)–C(28) Fragment

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