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Diels-Alder Reactions in Creating Complexity in Higher Order Isoprenoids: Proposed Biosynthesis and Biomimetic Total Syntheses

Journal

ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 7, Issue 8, Pages 1488-1501

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201800158

Keywords

abietanes; biomimetic synthesis; Diels-Alder reaction; icetaxanes; isoprenoids

Funding

  1. Science Engineering Research Board (SERB), Department of Science and Technology (DST) [CS-021/2014]
  2. SERB, DST, Govt. of INDIA [EMR/2016/000214]
  3. Council of Scientific and Industrial Research (CSIR), Govt. of India [02(0295)/17/EMR-II]

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Diels-Alder reactions and hetero Diels-Alder reactions play crucial role in building complexity in many naturally occurring isoprenoids. A number of structurally intriguing complex isoprenoids have been isolated form Nature, those are believed to follow a [4+2]-cycloaddition reaction in their biosynthetic proposal. In this focus review, we discuss on the recent efforts on biomimetic total syntheses of complex isoprenoids utilizing Diels-Alder and hetero Diels-Alder reactions. In particular, we have considered isoprenoids arising from a basic icetaxane, abietane, dinor-abietane, and abeo-abietane structural scaffolds.

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