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Literature DB >> 17078682

Synthesis of the entire framework of tartrolon B utilizing a silicon-tethered ring-closing metathesis strategy.

Abstract

[Structure: see text] A tandem ring-closing metathesis (RCM) of silaketal-tethered dienynes gives rise to bicyclic siloxanes, which upon removal of the silicon tether afford dienediol skeletons with a stereodefined E,Z-1,3-diene motif. The implementation of this methodology has led to the construction of the entire C1-C21 linear carbon skeleton of tartrolon B.

Entities: Chemical

Mesh：

Substances：

Year: 2006 PMID： 17078682 PMCID： PMC2518086 DOI： 10.1021/ol061952y

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

19 in total

Review 1. Enyne metathesis (enyne bond reorganization).

Authors: Steven T Diver; Anthony J Giessert
Journal: Chem Rev Date: 2004-03 Impact factor: 60.622

2. Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands.

Authors: M Scholl; S Ding; C W Lee; R H Grubbs
Journal: Org Lett Date: 1999-09-23 Impact factor: 6.005

3. Studies on marine microorganisms. V. A new antibiotic, aplasmomycin, produced by a streptomycete isolated from shallow sea mud.

Authors: Y Okami; T Okazaki; T Kitahara; H Umezawa
Journal: J Antibiot (Tokyo) Date: 1976-10 Impact factor: 2.649

4. Total synthesis of (-)-salicylihalamide.

Authors: A Fürstner; T Dierkes; O R Thiel; G Blanda
Journal: Chemistry Date: 2001-12-17 Impact factor: 5.236

5. Toward the synthesis of peloruside a: fragment synthesis and coupling studies.

Authors: Ian Paterson; M Emilia Di Francesco; Toralf Kühn
Journal: Org Lett Date: 2003-02-20 Impact factor: 6.005

6. Asymmetric induction in methyl ketone aldol additions to alpha-alkoxy and alpha,beta-bisalkoxy aldehydes: a model for acyclic stereocontrol.

Authors: David A Evans; Victor J Cee; Sarah J Siska
Journal: J Am Chem Soc Date: 2006-07-26 Impact factor: 15.419

Synthesis of the entire framework of tartrolon B utilizing a silicon-tethered ring-closing metathesis strategy.

Review 1. Enyne metathesis (enyne bond reorganization).

2. Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands.

3. Studies on marine microorganisms. V. A new antibiotic, aplasmomycin, produced by a streptomycete isolated from shallow sea mud.

4. Total synthesis of (-)-salicylihalamide.

5. Toward the synthesis of peloruside a: fragment synthesis and coupling studies.

6. Asymmetric induction in methyl ketone aldol additions to alpha-alkoxy and alpha,beta-bisalkoxy aldehydes: a model for acyclic stereocontrol.

7. Efficient synthesis of alkynylsilyl ethers and silaketals via base-induced alkynylsilane alcoholysis.

8. Total synthesis of the boron-containing ion carrier antibiotic macrodiolide tartrolon B.

9. The tartrolons, new boron-containing antibiotics from a myxobacterium, Sorangium cellulosum.

10. 1,5-asymmetric induction in boron-mediated beta-alkoxy methyl ketone aldol addition reactions.

1. Application of tandem ring-closing enyne metathesis: formal total synthesis of (-)-cochleamycin A.

2. Synthesis of cyclic alkenylsiloxanes by semihydrogenation: a stereospecific route to (Z)-alkenyl polyenes.