Toward the total synthesis of grayanane diterpene mollanol A by a Prins [3 + 2] strategy

Literature Information

Publication Date 2020-02-15
DOI 10.1039/D0OB00160K
Impact Factor 3.876
Authors

Jianzhuang Miao, Yi-Xuan Zheng, Shi-Chao Lu, Shi-Peng Zhang, Ya-Ling Gong, Shu Xu


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Abstract

Toward the total synthesis of a novel grayanoid, mollanol A, we developed a concise convergent strategy based on a formal [3 + 2] cyclization initiated by the Prins reaction. In this key intermolecular reaction between an unprotected hydroxyaldehyde and activating-group-free olefins, two chiral carbons and one densely substituted tetrahydrofuran ring were constructed stereoselectively.

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Source Journal

Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
Self-citation Rate: 10.3%
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Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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