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Literature DB >> 19241430

Total synthesis of sporolide B.

K C Nicolaou¹, Yefeng Tang, Jianhua Wang.

Abstract

An ocean of discovery: The first total synthesis of the highly oxygenated, marine-derived, natural product sporolide B has been achieved through a convergent strategy. The key steps involve a ruthenium-catalyzed [2+2+2] cycloaddition to assemble the indene structural motif and a thermally induced Diels-Alder-type reaction to forge the macrocycle (see scheme).

Entities: Chemical Disease Species

Mesh：

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Year: 2009 PMID： 19241430 PMCID： PMC2674522 DOI： 10.1002/anie.200900264

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

8 in total

1. Sporolides A and B: structurally unprecedented halogenated macrolides from the marine actinomycete Salinispora tropica.

Authors: Greg O Buchanan; Philip G Williams; Robert H Feling; Christopher A Kauffman; Paul R Jensen; William Fenical
Journal: Org Lett Date: 2005-06-23 Impact factor: 6.005

2. Developing a new resource for drug discovery: marine actinomycete bacteria.

Authors: William Fenical; Paul R Jensen
Journal: Nat Chem Biol Date: 2006-12 Impact factor: 15.040

3. Nucleophilic addition to a p-benzyne derived from an enediyne: a new mechanism for halide incorporation into biomolecules.

Authors: Charles L Perrin; Betsy L Rodgers; Joseph M O'Connor
Journal: J Am Chem Soc Date: 2007-03-23 Impact factor: 15.419

Review 4. Chemistry and biology of natural and designed enediynes.

Authors: K C Nicolaou; A L Smith; E W Yue
Journal: Proc Natl Acad Sci U S A Date: 1993-07-01 Impact factor: 11.205

5. Ruthenium(II)-catalyzed selective intramolecular [2 + 2 + 2] alkyne cyclotrimerizations.

Authors: Yoshihiko Yamamoto; Takayasu Arakawa; Ryuji Ogawa; Kenji Itoh
Journal: J Am Chem Soc Date: 2003-10-08 Impact factor: 15.419

6. Synthesis of the sporolide ring framework through a cascade sequence involving an intramolecular [4+2] cycloaddition reaction of an o-quinone.

Authors: K C Nicolaou; Jianhua Wang; Yefeng Tang
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

7. Unraveling the biosynthesis of the sporolide cyclohexenone building block.

Authors: Ryan P McGlinchey; Markus Nett; Bradley S Moore
Journal: J Am Chem Soc Date: 2008-01-31 Impact factor: 15.419

8. Genome sequencing reveals complex secondary metabolome in the marine actinomycete Salinispora tropica.

Authors: Daniel W Udwary; Lisa Zeigler; Ratnakar N Asolkar; Vasanth Singan; Alla Lapidus; William Fenical; Paul R Jensen; Bradley S Moore
Journal: Proc Natl Acad Sci U S A Date: 2007-06-11 Impact factor: 11.205

8 in total

11 in total

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors: K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal: Chem Soc Rev Date: 2012-06-28 Impact factor: 54.564

2. Formal [2 + 2 + 2] cycloaddition strategy based on an intramolecular propargylic ene reaction/Diels-Alder cycloaddition cascade.

Authors: Julia M Robinson; Takeo Sakai; Katsuhiko Okano; Takafumi Kitawaki; Rick L Danheiser
Journal: J Am Chem Soc Date: 2010-08-18 Impact factor: 15.419

Total synthesis of sporolide B.

1. Sporolides A and B: structurally unprecedented halogenated macrolides from the marine actinomycete Salinispora tropica.

2. Developing a new resource for drug discovery: marine actinomycete bacteria.

3. Nucleophilic addition to a p-benzyne derived from an enediyne: a new mechanism for halide incorporation into biomolecules.

Review 4. Chemistry and biology of natural and designed enediynes.

5. Ruthenium(II)-catalyzed selective intramolecular [2 + 2 + 2] alkyne cyclotrimerizations.

6. Synthesis of the sporolide ring framework through a cascade sequence involving an intramolecular [4+2] cycloaddition reaction of an o-quinone.

7. Unraveling the biosynthesis of the sporolide cyclohexenone building block.

8. Genome sequencing reveals complex secondary metabolome in the marine actinomycete Salinispora tropica.

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

2. Formal [2 + 2 + 2] cycloaddition strategy based on an intramolecular propargylic ene reaction/Diels-Alder cycloaddition cascade.

3. Metallacycle-Mediated Cross-Coupling in Natural Product Synthesis.

4. Sporolide B: Synthetic Studies.

5. Total synthesis of sporolide B and 9-epi-sporolide B.

6. Convergent synthesis and structural confirmation of phellodonin and sarcodonin ε.

Review 7. Ruthenium-Catalyzed Cycloadditions to Form Five-, Six-, and Seven-Membered Rings.

Review 8. Unconventional Macrocyclizations in Natural Product Synthesis.

Review 9. A Review: Halogenated Compounds from Marine Actinomycetes.

10. Enantioselective Total Synthesis of (+)-Heilonine.