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16-Step Synthesis of the Isoryanodane Diterpene (+)-Perseanol

Han, Arthur and Tao, Yujia and Reisman, Sarah E. (2019) 16-Step Synthesis of the Isoryanodane Diterpene (+)-Perseanol. . (Unpublished) http://resolver.caltech.edu/CaltechAUTHORS:20190610-080930538

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Abstract

(+)-Perseanol is an isoryanodane diterpene with potent antifeedant and insecticidal properties isolated from the tropical shrub Persea indica. Here we report the first chemical synthesis of (+)-perseanol, which proceeds in 16 steps from commercially available (R)-pulegone. The synthesis features a two-step annulation process that rapidly assembles the tetracyclic core from readily accessible cyclopentyl building blocks. This work demonstrates how convergent fragment coupling, when combined with strategic oxidation tactics, can enable the concise synthesis of complex and highly oxidized diterpene natural products.


Item Type:Report or Paper (Discussion Paper)
Related URLs:
URLURL TypeDescription
https://chemrxiv.org/articles/16-Step_Synthesis_of_the_Isoryanodane_Diterpene_-Perseanol/8100152OrganizationDiscussion Paper
ORCID:
AuthorORCID
Han, Arthur0000-0001-8691-699X
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:CC BY-NC-ND 4.0. Submission date: 20.05.2019; First online date: Posted date 21.05.2019 Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis are gratefully acknowledged for access to analytical equipment. We thank Mr. Larry Henling (Caltech) and Dr. Julie Hofstra (Caltech) for X-ray data collection and data refinement, respectively, for the structure of 32 and S21. Prof. Yonghui Zhang (Huanzhong University of Science and Technology) is acknowledged for providing original spectral data of perseanol. Dr. Kangway Chuang (Caltech) is gratefully acknowledged for insightful contributions to the synthetic design. Fellowship support was provided by the NIH (A.H., Nos. 5T32GM007616-37 and 1F31GM120821). S.E.R. is a Heritage Medical Research Investigator. Financial support from the NIH (Nos. NIGMS RGM097582-01 and R35GM118191-01), Eli Lilly, and Novartis is gratefully acknowledged. Author Contributions. A.H. and S.E.R. conceived this work; A.H., Y.T., and S.E.R. designed the experiments and analyzed the data; A.H. and Y.T. conducted the experiments; A.H. and S.E.R. wrote the manuscript. No conflict of Interest.
Group:Heritage Medical Research Institute
Funders:
Funding AgencyGrant Number
NIH Predoctoral Fellowship5T32GM007616-37
NIH Postdoctoral Fellowship1F31GM120821
NIHRGM097582-01
NIHR35GM118191-01
Eli LillyUNSPECIFIED
NovartisUNSPECIFIED
Subject Keywords:perseanol; total synthesis; isoryanodane; Pd-catalyzed
Record Number:CaltechAUTHORS:20190610-080930538
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20190610-080930538
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:96224
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:10 Jun 2019 17:42
Last Modified:10 Jul 2019 00:05

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