Synthetic Studies toward the Total Synthesis of Scabrolide A

Herein, we report a concise route to the [5-5-6]-fused tricyclic core of scabrolide A and our efforts toward the construction of the fourth cycloheptane ring of the molecule via a 7-<i>endo-trig</i> radical cyclization. The tricyclic cyclohexenone core was assembled by a ring-closing metathesis (RCM) reaction followed by oxidation and concomitant isomerization of the double bond. These promising results have potential implications in the synthesis of similar tricyclic cores of many other congeners within this family of furanobutenolide-derived polycyclic cembranoids and norcembranoids.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-04-16
DOI
https://doi.org/10.1021/acs.joc.5c00298
Primary Topic
Synthetic Organic Chemistry Methods
Type
article
Field-Weighted Citation Impact
0.00

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article

Synthetic Studies toward the Total Synthesis of Scabrolide A

Sabnam Begum, Tushar Kanti Chakraborty
The Journal of Organic Chemistry
Synthetic Organic Chemistry Methods
article

Synthetic Studies toward the Total Synthesis of Scabrolide A

Sabnam Begum, Tushar Kanti Chakraborty
article en

Abstract

Herein, we report a concise route to the [5-5-6]-fused tricyclic core of scabrolide A and our efforts toward the construction of the fourth cycloheptane ring of the molecule via a 7-<i>endo-trig</i> radical cyclization. The tricyclic cyclohexenone core was assembled by a ring-closing metathesis (RCM) reaction followed by oxidation and concomitant isomerization of the double bond. These promising results have potential implications in the synthesis of similar tricyclic cores of many other congeners within this family of furanobutenolide-derived polycyclic cembranoids and norcembranoids.

The Journal of Organic ChemistryVol. 90(16)
Indian Institute of Science Bangalore (IN)
Indian Institute of Science, Indian National Science Academy, Council of Scientific and Industrial Research, India
Zero hunger
Openalex Percentile: Top 94%
Synthetic Organic Chemistry Methods
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