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Literature DB >> 16092840

Stereoselective assembly of a 1,3-diene via coupling between an allenic acetate and a (B)-alkylborane: synthetic studies on amphidinolide B1.

Amit K Mandal¹, John S Schneekloth, Craig M Crews.

Abstract

The preparation of three fragments for the total synthesis of amphidinolide B1 has been described. The C16 stereochemistry was set by asymmetric allylic alkylation. C21 and C25 stereogenic centers were set by an enantioselective/diastereoselective double allylation reaction. The C9 configuration was set by an asymmetric heteroene reaction. A differentially substituted stereodefined 1,3-diene iodide was synthesized by iodide-mediated S(N)2' reaction. A novel stereoselective method to assemble a 1,3-diene by coupling an allenic acetate and (B)-alkylborane is also reported. [structure: see text]

Entities: Chemical Gene

Mesh：

Substances：

Year: 2005 PMID： 16092840 PMCID： PMC2507736 DOI： 10.1021/ol051175m

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

8 in total

1. Unified synthesis of C19-C26 subunits of amphidinolides B1, B2, and B3 by exploiting unexpected stereochemical differences in Crimmins' and Evans' aldol reactions.

Authors: Wei Zhang; Rich G Carter; Alexandre F T Yokochi
Journal: J Org Chem Date: 2004-04-02 Impact factor: 4.354

2. Silyl ketone chemistry. Preparation and reactions of silyl allenol ethers. Diels-Alder reaction of siloxy vinylallenes leading to sesquiterpenes.

Authors: H J Reich; E K Eisenhart; R E Olson; M J Kelly
Journal: J Am Chem Soc Date: 1986-11-01 Impact factor: 15.419

3. Cytotoxic macrolides from a cultured marine dinoflagellate of the genus Amphidinium.

Authors: J Kobayashi; M Ishibashi; H Nakamura; Y Ohizumi; T Yamasu; Y Hirata; T Sasaki; T Ohta; S Nozoe
Journal: J Nat Prod Date: 1989 Sep-Oct Impact factor: 4.050

4. The B-Alkyl Suzuki-Miyaura Cross-Coupling Reaction: Development, Mechanistic Study, and Applications in Natural Product Synthesis A list of abbreviations can be found at the end of the article.

Authors: Sherry R. Chemler; Dirk Trauner; Samuel J. Danishefsky
Journal: Angew Chem Int Ed Engl Date: 2001-12-17 Impact factor: 15.336

Review 5. Chemistry of potent anti-cancer compounds, amphidinolides.

Authors: T K Chakraborty; S Das
Journal: Curr Med Chem Anticancer Agents Date: 2001-08

6. Palladium(II)-catalyzed S(N)2' reactions of alpha-allenic acetates. Stereoconvergent synthesis of (Z,E)-2-bromo-1,3-dienes.

Authors: A Horváth; J E Bäckvall
Journal: J Org Chem Date: 2001-11-30 Impact factor: 4.354

7. Enantioselective synthesis of 1,5-anti- and 1,5-syn-diols using a highly diastereoselective one-pot double allylboration reaction sequence.

Authors: Eric M Flamme; William R Roush
Journal: J Am Chem Soc Date: 2002-11-20 Impact factor: 15.419

Review 8. Amphidinolides, bioactive macrolides from symbiotic marine dinoflagellates.

Authors: Jun'ichi Kobayashi; Masashi Tsuda
Journal: Nat Prod Rep Date: 2004-01-07 Impact factor: 13.423

8 in total

6 in total

Stereoselective assembly of a 1,3-diene via coupling between an allenic acetate and a (B)-alkylborane: synthetic studies on amphidinolide B1.

1. Unified synthesis of C19-C26 subunits of amphidinolides B1, B2, and B3 by exploiting unexpected stereochemical differences in Crimmins' and Evans' aldol reactions.

2. Silyl ketone chemistry. Preparation and reactions of silyl allenol ethers. Diels-Alder reaction of siloxy vinylallenes leading to sesquiterpenes.

3. Cytotoxic macrolides from a cultured marine dinoflagellate of the genus Amphidinium.

4. The B-Alkyl Suzuki-Miyaura Cross-Coupling Reaction: Development, Mechanistic Study, and Applications in Natural Product Synthesis A list of abbreviations can be found at the end of the article.

Review 5. Chemistry of potent anti-cancer compounds, amphidinolides.

6. Palladium(II)-catalyzed S(N)2' reactions of alpha-allenic acetates. Stereoconvergent synthesis of (Z,E)-2-bromo-1,3-dienes.

7. Enantioselective synthesis of 1,5-anti- and 1,5-syn-diols using a highly diastereoselective one-pot double allylboration reaction sequence.

Review 8. Amphidinolides, bioactive macrolides from symbiotic marine dinoflagellates.

1. Synthetic studies on amphidinolide B1.

2. Synthesis of the C3-C18 fragment of amphidinolides G and H.

3. Total synthesis of cytotoxic macrolide amphidinolide B1 and the proposed structure of amphidinolide B2.

4. Amphidinolide B: total synthesis, structural investigation, and biological evaluation.

5. Synthetic studies toward amphidinolide B1: synthesis of the C9-C26 fragment.

6. Efficient synthesis of the C(7)-C(20) subunit of amphidinolides C and F.