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Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

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Updated: Jun 8, 2026

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

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Published on: February 6, 2019

Convergent route to the spirohexenolide macrocycle.

Brian D Jones¹, James J La Clair, Curtis E Moore

¹Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, USA.

Organic Letters

|September 21, 2010

Summary

This study details a novel three-component synthesis for spirohexenolides, utilizing key reactions like 1,2-addition and Stille coupling. The strategy enables the construction of complex macrocycles, including progress toward (±)-spirohexenolide B.

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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Published on: February 7, 2019

Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Spirohexenolides are a class of complex natural products with potential biological activity.
Efficient synthetic routes are crucial for accessing these molecules and their analogs.

Purpose of the Study:

To develop a novel and efficient three-component strategy for the synthesis of spirohexenolides.
To demonstrate the application of this strategy in the total synthesis of (±)-spirohexenolide B.

Main Methods:

A three-component strategy involving 1,2-addition to form the C2-C3 bond.
Stille coupling to incorporate a sulfone-containing component.
Intramolecular Julia-Kocienski reaction for macrocycle formation and trans-olefin installation.

Main Results:

Successful development of a convergent synthetic route to spirohexenolides.
Demonstration of key bond formations including C-C and C-O bonds.
Progress made towards the total synthesis of (±)-spirohexenolide B.

Conclusions:

The presented three-component strategy offers an efficient approach to spirohexenolide synthesis.
This methodology can be applied to the synthesis of other complex macrocyclic compounds.
Further studies can explore analogs and biological activities of synthesized compounds.