CaltechAUTHORS
Published May 13, 2020 | Version Supplemental Material + Submitted
Journal Article Open

The Total Synthesis of (–)-Scabrolide A

Creators

  • 1. ROR icon California Institute of Technology

Abstract

The first total synthesis of the norcembranoid diterpenoid scabrolide A is disclosed. The route begins with the synthesis of two chiral pool-derived fragments, which undergo a convergent coupling to expediently introduce all 19 carbon atoms of the natural product. An intramolecular Diels–Alder reaction and an enone–olefin cycloaddition/fragmentation sequence are then employed to construct the fused [5–6–7] linear carbocyclic core of the molecule and complete the total synthesis.

Additional Information

© 2020 American Chemical Society. Received: March 3, 2020; Published: March 30, 2020. The authors wish to thank NSF (CHE-1800511) as well as Caltech for funding this research. B.P.P. additionally thanks NSF for support in the form of a predoctoral fellowship. The authors thank Dr. David VanderVelde for NMR assistance and maintenance of the Caltech NMR facility as well as Max Kaiser for assistance with NMR interpretation, Dr. Michael Takase and Lawrence Henling for XRD assistance, and Dr. Mona Shahgholi and Naseem Torian for mass spectrometry assistance. Additionally, the authors would like to thank Prof. Jyh-Horng Sheu for kindly providing ¹H and ¹³C NMR spectra of isolated scabrolide A. Author Contributions: N.J.H. and S.A.L. contributed equally. The authors declare no competing financial interest.

Attached Files

Submitted - The_Total_Synthesis_of____-Scabrolide_a_v1.pdf

Supplemental Material - ScabrolideSIFinal.pdf

Supplemental Material - TOCGraphic.pdf

Supplemental Material - ja0c02513_si_002.cif

Supplemental Material - ja0c02513_si_003.cif

Supplemental Material - ja0c02513_si_004.cif

Supplemental Material - ja0c02513_si_005.cif

Supplemental Material - ja0c02513_si_006.pdf

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Additional details

Identifiers

Eprint ID
101705
Resolver ID
CaltechAUTHORS:20200304-101308383

Related works

Describes
10.26434/chemrxiv.11923632.v1 (DOI)

Funding

NSF
CHE-1800511
Caltech
NSF Predoctoral Fellowship

Dates

Created
2020-03-04
Created from EPrint's datestamp field
Updated
2023-06-01
Created from EPrint's last_modified field