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Literature DB >> 15101758

Efficient and selective synthesis of siphonarienolone and related reduced polypropionates via Zr-catalyzed asymmetric carboalumination.

Marina Magnin-Lachaux¹, Ze Tan, Bo Liang, Ei-Ichi Negishi.

Abstract

[reaction: see text] Siphonarienolone (1) has been synthesized from siphonarienal (3) in 66% over four steps. Synthesis of 3, in turn, has been achieved in two steps (85% combined yield) from 4, prepared from 3-buten-1-ol in seven steps (23% combined yield). Also, a two-step conversion of 3 into siphonarienone (2) is reported.

Entities: Chemical

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Year: 2004 PMID： 15101758 DOI： 10.1021/ol0497483

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

9 in total

1. Fully reagent-controlled asymmetric synthesis of (-)-spongidepsin via the Zr-catalyzed asymmetric carboalumination of alkenes (ZACA reaction).

Authors: Gangguo Zhu; Ei-ichi Negishi
Journal: Org Lett Date: 2007-06-21 Impact factor: 6.005

2. Efficient and selective syntheses of (all-E)- and (6E,10Z)-2'-O-methylmyxalamides D via Pd-catalyzed alkenylation--carbonyl olefination synergy.

Authors: Guangwei Wang; Zhihong Huang; Ei-Ichi Negishi
Journal: Org Lett Date: 2008-07-02 Impact factor: 6.005

3. Widely applicable synthesis of enantiomerically pure tertiary alkyl-containing 1-alkanols by zirconium-catalyzed asymmetric carboalumination of alkenes and palladium- or copper-catalyzed cross-coupling.

Authors: Shiqing Xu; Ching-Tien Lee; Guangwei Wang; Ei-ichi Negishi
Journal: Chem Asian J Date: 2013-05-13

4. Efficient and stereoselective synthesis of yellow scale pheromone via alkyne haloboration, Zr-catalyzed asymmetric carboalumination of alkenes (ZACA reaction), and Pd-catalyzed tandem Negishi coupling.

Authors: Zhaoqing Xu; Ei-Ichi Negishi
Journal: Org Lett Date: 2008-09-03 Impact factor: 6.005

9. Structure elucidation of female-specific volatiles released by the parasitoid wasp Trichogramma turkestanica (Hymenoptera: Trichogrammatidae).

Authors: Armin Tröger; Teris A van Beek; Martinus E Huigens; Isabel M M S Silva; Maarten A Posthumus; Wittko Francke
Journal: Beilstein J Org Chem Date: 2014-04-02 Impact factor: 2.883

9 in total

Efficient and selective synthesis of siphonarienolone and related reduced polypropionates via Zr-catalyzed asymmetric carboalumination.

1. Fully reagent-controlled asymmetric synthesis of (-)-spongidepsin via the Zr-catalyzed asymmetric carboalumination of alkenes (ZACA reaction).

2. Efficient and selective syntheses of (all-E)- and (6E,10Z)-2'-O-methylmyxalamides D via Pd-catalyzed alkenylation--carbonyl olefination synergy.

3. Widely applicable synthesis of enantiomerically pure tertiary alkyl-containing 1-alkanols by zirconium-catalyzed asymmetric carboalumination of alkenes and palladium- or copper-catalyzed cross-coupling.

4. Efficient and stereoselective synthesis of yellow scale pheromone via alkyne haloboration, Zr-catalyzed asymmetric carboalumination of alkenes (ZACA reaction), and Pd-catalyzed tandem Negishi coupling.

Review 5. Catalytic Enantioselective Functionalization of Unactivated Terminal Alkenes.

Review 6. Bioinspired iterative synthesis of polyketides.

Review 7. Catalytic enantioselective synthesis of chiral organic compounds of ultra-high purity of >99% ee.

8. Bioinspired Asymmetric Total Synthesis of Emeriones A-C.

9. Structure elucidation of female-specific volatiles released by the parasitoid wasp Trichogramma turkestanica (Hymenoptera: Trichogrammatidae).