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Literature DB >> 16435880

Total synthesis of (+/-)-bipinnatin J.

Abstract

[reaction: see text]. The total synthesis of (+/-)-bipinnatin J was achieved through a concise route that features the use of a silver ion promoted S(N)1-type gamma-alkylation of a siloxyfuran and a diastereoselective Cr(II)-mediated macrocyclization to provide bipinnatin J (1), wherein the remote furanone stereocenter at C10 induced the relative stereochemistry of the two additional stereocenters.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2006 PMID： 16435880 PMCID： PMC2537461 DOI： 10.1021/ol053054s

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

20 in total

1. The First Cembrane-Pseudopterane Cycloisomerization.

Authors: Abimael D. Rodríguez; Jian-Gong Shi
Journal: J Org Chem Date: 1998-02-06 Impact factor: 4.354

Review 2. Marine natural products.

Authors: D John Faulkner
Journal: Nat Prod Rep Date: 2002-02 Impact factor: 13.423

3. Isolation, structure elucidation, and synthesis of bisgersolanolide, a novel heptacyclic bis-diterpenoid from the gorgonian octocoral Pseudopterogorgia bipinnata.

Authors: A D Rodríguez; J G Shi
Journal: Org Lett Date: 1999-07-29 Impact factor: 6.005

4. Quantal analysis indicates an alpha-toxin-like block by lophotoxin, a non-ionic marine natural product.

Authors: R B Langdon; R S Jacobs
Journal: Life Sci Date: 1983-03-14 Impact factor: 5.037

5. Synthesis of (-)-deoxypukalide, the enantiomer of a degradation product of the furanocembranolide pukalide.

Authors: J A Marshall; E A Van Devender
Journal: J Org Chem Date: 2001-11-30 Impact factor: 4.354

6. Palladium-Catalyzed Cross-Coupling of 2,5-Cyclohexadienyl-Substituted Aryl or Vinylic Iodides and Carbon or Heteroatom Nucleophiles.

Authors: Richard C. Larock; Xiaojun Han
Journal: J Org Chem Date: 1999-03-19 Impact factor: 4.354

7. Highly oxygenated pseudopterane and cembranolide diterpenes from the Caribbean sea feather Pseudopterogorgia bipinnata.

Authors: A D Rodríguez; J G Shi; S D Huang
Journal: J Nat Prod Date: 1999-09 Impact factor: 4.050

8. Stereoselective construction of a beta-isopropenyl alcohol moiety at the C(2) and (3) of kallolide A and pinnatin a using a [2,3] Wittig rearrangement of cyclic furfuryl ethers.

Authors: Masayoshi Tsubuki; Kazunori Takahashi; Toshio Honda
Journal: J Org Chem Date: 2003-12-26 Impact factor: 4.354

9. Irreversible inhibitors of nicotinic acetylcholine receptors: isolation and structural characterization of the biologically active solvolysis products of bipinnatin-A and bipinnatin-C.

Authors: E G Hyde; A Boyer; P Tang; Y Xu; S N Abramson
Journal: J Med Chem Date: 1995-06-09 Impact factor: 7.446

Total synthesis of (+/-)-bipinnatin J.

1. The First Cembrane-Pseudopterane Cycloisomerization.

Review 2. Marine natural products.

3. Isolation, structure elucidation, and synthesis of bisgersolanolide, a novel heptacyclic bis-diterpenoid from the gorgonian octocoral Pseudopterogorgia bipinnata.

4. Quantal analysis indicates an alpha-toxin-like block by lophotoxin, a non-ionic marine natural product.

5. Synthesis of (-)-deoxypukalide, the enantiomer of a degradation product of the furanocembranolide pukalide.

6. Palladium-Catalyzed Cross-Coupling of 2,5-Cyclohexadienyl-Substituted Aryl or Vinylic Iodides and Carbon or Heteroatom Nucleophiles.

7. Highly oxygenated pseudopterane and cembranolide diterpenes from the Caribbean sea feather Pseudopterogorgia bipinnata.

8. Stereoselective construction of a beta-isopropenyl alcohol moiety at the C(2) and (3) of kallolide A and pinnatin a using a [2,3] Wittig rearrangement of cyclic furfuryl ethers.

9. Irreversible inhibitors of nicotinic acetylcholine receptors: isolation and structural characterization of the biologically active solvolysis products of bipinnatin-A and bipinnatin-C.

10. Lophotoxin-insensitive nematode nicotinic acetylcholine receptors.

1. ω-Hydroxy isoprenoid bisphosphonates as linkable GGDPS inhibitors.

2. A strategy toward the synthesis of C₁₃-oxidized cembrenolides.

3. Synthesis of a highly functionalized core of verrillin.

4. Total synthesis of norcembrenolide B and scabrolide D.

5. Short, enantioselective total synthesis of chatancin.