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Literature DB >> 11878938

The total synthesis of (+/-)-merrilactone A.

Vladimir B Birman¹, Samuel J Danishefsky.

Abstract

The total synthesis of the title compound has been accomplished in 20 steps. The key step is a free radical cyclization of vinyl bromide 29 to afford 30. The synthesis also features an efficient Dielsminus signAlder reaction of 2,3-dimethylmaleic anhydride with 1-(tert-butyldimethylsiloxy)-butadiene. The oxetane moiety of merrilactone A is fashioned via a Payne-like rearrangement of a hydroxyepoxide (see 2 right arrow 1).

Entities: Chemical

Mesh：

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Year: 2002 PMID： 11878938 DOI： 10.1021/ja012495d

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

18 in total

Review 1. Neurotrophic natural products: chemistry and biology.

Authors: Jing Xu; Michelle H Lacoske; Emmanuel A Theodorakis
Journal: Angew Chem Int Ed Engl Date: 2013-12-18 Impact factor: 15.336

2. Development of a Terpene Feedstock-Based Oxidative Synthetic Approach to the Illicium Sesquiterpenes.

Authors: Kevin Hung; Matthew L Condakes; Luiz F T Novaes; Stephen J Harwood; Takahiro Morikawa; Zhi Yang; Thomas J Maimone
Journal: J Am Chem Soc Date: 2019-02-11 Impact factor: 15.419

3. Synthesis of Neurotrophic Seco-prezizaane Sesquiterpenes (1R,10S)-2-Oxo-3,4-dehydroneomajucin, (2S)-Hydroxy-3,4-dehydroneomajucin, and (-)-Jiadifenin.

Authors: Xiayun Cheng; Glenn C Micalizio
Journal: J Am Chem Soc Date: 2016-01-25 Impact factor: 15.419

4. The enantioselective construction of tetracyclic diterpene skeletons with Friedel-Crafts alkylation and palladium-catalyzed cycloalkenylation reactions.

Authors: Sarah J Burke; William P Malachowski; Sharan K Mehta; Roselyn Appenteng
Journal: Org Biomol Chem Date: 2015-03-07 Impact factor: 3.876

The total synthesis of (+/-)-merrilactone A.

Review 1. Neurotrophic natural products: chemistry and biology.

2. Development of a Terpene Feedstock-Based Oxidative Synthetic Approach to the Illicium Sesquiterpenes.

3. Synthesis of Neurotrophic Seco-prezizaane Sesquiterpenes (1R,10S)-2-Oxo-3,4-dehydroneomajucin, (2S)-Hydroxy-3,4-dehydroneomajucin, and (-)-Jiadifenin.

4. The enantioselective construction of tetracyclic diterpene skeletons with Friedel-Crafts alkylation and palladium-catalyzed cycloalkenylation reactions.

5. Stereodivergent Attached-Ring Synthesis via Non-Covalent Interactions: A Short Formal Synthesis of Merrilactone A.

6. Oxidative Entry into the Illicium Sesquiterpenes: Enantiospecific Synthesis of (+)-Pseudoanisatin.

7. Illicium sesquiterpenes: divergent synthetic strategy and neurotrophic activity studies.

8. Total synthesis of (±)-maoecrystal V.

Review 9. Total synthesis of complex terpenoids employing radical cascade processes.

Review 10. Catalytic enantioselective construction of vicinal quaternary carbon stereocenters.