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Total synthesis of (+)-ar-macrocarpene.

Arindam Khatua1, Sovan Niyogi1, Vishnumaya Bisai2

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This study presents the first catalytic asymmetric synthesis of (+)-ar-macrocarpene, a sesquiterpene, using a novel 7-step strategy. The method achieves high yields and enantioselectivity, offering an efficient route to this complex molecule.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Natural Product Synthesis

Background:

  • Sesquiterpenes are a class of terpenoids with diverse biological activities.
  • The total synthesis of complex natural products like (+)-ar-macrocarpene is crucial for chemical research and drug discovery.
  • Developing efficient and stereoselective synthetic routes remains a significant challenge in organic chemistry.

Purpose of the Study:

  • To achieve the first catalytic asymmetric total synthesis of the sesquiterpene (+)-ar-macrocarpene.
  • To develop an efficient and stereoselective synthetic strategy from readily available starting materials.
  • To explore novel synthetic methodologies, including key rearrangements and reductions.

Main Methods:

  • The synthesis employs a 7-step sequence starting from 5,5-dimethylcyclohexane-1,3-dione.
  • A key step involves a [3,3]-sigmatropic rearrangement via allylic diazene rearrangement (ADR) under Mitsunobu conditions.
  • Enantioselective reduction using Corey-Bakshi-Shibata conditions establishes the critical stereocenter.

Main Results:

  • The total synthesis of (+)-ar-macrocarpene was successfully accomplished in 7 steps.
  • An overall yield of 42.1% was achieved from inexpensive starting materials.
  • The enantioselective reduction provided the allylic alcohol intermediate with high enantiopurity (95% ee).

Conclusions:

  • This work demonstrates a novel and efficient catalytic asymmetric total synthesis of (+)-ar-macrocarpene.
  • The developed strategy highlights the utility of allylic diazene rearrangement and enantioselective reduction in complex molecule synthesis.
  • This synthesis provides a valuable pathway for accessing sesquiterpenes and related compounds.