Literature DB >> 19810767

Silyl-substituted spirodiepoxides: stereoselective formation and regioselective opening.

Partha Ghosh1, Joseph R Cusick, Jennifer Inghrim, Lawrence J Williams.   

Abstract

A short synthesis of the natural product epi-citreodiol and the method developed to gain access to this target are described. Key advances focus on silyl substituted allenes. Upon exposure to dimethyldioxirane, spirodiepoxides form with high face selectivity and subsequently react at the silyl terminus.

Entities:  

Mesh：

Substances：

Year:  2009        PMID： 19810767      PMCID： PMC3047402          DOI： 10.1021/ol901948d

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


  11 in total

1.  Ladder polyether synthesis via epoxide-opening cascades using a disappearing directing group.

Authors:  Graham L Simpson; Timothy P Heffron; Estíbaliz Merino; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2006-02-01       Impact factor: 15.419

2.  Spirodiepoxide reaction with cuprates.

Authors:  Partha Ghosh; Stephen D Lotesta; Lawrence J Williams
Journal:  J Am Chem Soc       Date:  2007-02-09       Impact factor: 15.419

3.  Discovery of incednine as a potent modulator of the anti-apoptotic function of Bcl-xL from microbial origin.

Authors:  Yushi Futamura; Ryuichi Sawa; Yoji Umezawa; Masayuki Igarashi; Hikaru Nakamura; Kimiko Hasegawa; Mikio Yamasaki; Etsu Tashiro; Yoshikazu Takahashi; Yuzuru Akamatsu; Masaya Imoto
Journal:  J Am Chem Soc       Date:  2008-01-19       Impact factor: 15.419

4.  Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density.

Authors: 
Journal:  Phys Rev B Condens Matter       Date:  1988-01-15

5.  The structure of pikromycin.

Authors:  H Muxfeldt; S Shrader; P Hansen; H Brockman
Journal:  J Am Chem Soc       Date:  1968-08-14       Impact factor: 15.419

6.  Effects of solvents and water in Ti(III)-mediated radical cyclizations of epoxygermacrolides. Straightforward synthesis and absolute stereochemistry of (+)-3alpha-hydroxyreynosin and related eudesmanolides.

Authors:  Alejandro F Barrero; J Enrique Oltra; Juan M Cuerva; Antonio Rosales
Journal:  J Org Chem       Date:  2002-04-19       Impact factor: 4.354

7.  Spirodiepoxides in total synthesis: epoxomicin.

Authors:  Sreenivas Katukojvala; Kristin N Barlett; Stephen D Lotesta; Lawrence J Williams
Journal:  J Am Chem Soc       Date:  2004-12-01       Impact factor: 15.419

8.  A formal synthesis of psymberin.

Authors:  Ning Shangguan; Sezgin Kiren; Lawrence J Williams
Journal:  Org Lett       Date:  2007-02-24       Impact factor: 6.005

9.  A spirodiepoxide-based strategy to the A-B ring system of pectenotoxin 4.

Authors:  Stephen D Lotesta; Yongquan Hou; Lawrence J Williams
Journal:  Org Lett       Date:  2007-02-08       Impact factor: 6.005

10.  Accurate determinations of the extent to which the SE2' reactions of allyl-, allenyl- and propargylsilanes are stereospecifically anti.

Authors:  Michael J C Buckle; Ian Fleming; Salvador Gil; Kah Ling Christine Pang
Journal:  Org Biomol Chem       Date:  2004-02-09       Impact factor: 3.876
View more
  11 in total

1.  Total synthesis of (±)-rocaglamide via oxidation-initiated Nazarov cyclization.

Authors:  John A Malona; Kevin Cariou; William T Spencer; Alison J Frontier
Journal:  J Org Chem       Date:  2012-01-26       Impact factor: 4.354

2.  Spirodiepoxide-based cascades: direct access to diverse motifs.

Authors:  Rojita Sharma; Madhuri Manpadi; Yue Zhang; Hiyun Kim; Novruz G Ahkmedov; Lawrence J Williams
Journal:  Org Lett       Date:  2011-06-07       Impact factor: 6.005

3.  Modular functionalization of allenes to aminated stereotriads.

Authors:  Christopher S Adams; Luke A Boralsky; Ilia A Guzei; Jennifer M Schomaker
Journal:  J Am Chem Soc       Date:  2012-06-20       Impact factor: 15.419

4.  Oxidation-initiated Nazarov cyclization of vinyl alkoxyallenes.

Authors:  William T Spencer; Mark D Levin; Alison J Frontier
Journal:  Org Lett       Date:  2010-12-14       Impact factor: 6.005

5.  Blockage of the early step of lankacidin biosynthesis caused a large production of pentamycin, citreodiol and epi-citreodiol in Streptomyces rochei.

Authors:  Zhisheng Cao; Ryuhei Yoshida; Haruyasu Kinashi; Kenji Arakawa
Journal:  J Antibiot (Tokyo)       Date:  2014-12-03       Impact factor: 2.649

6.  Allene functionalization via bicyclic methylene aziridines.

Authors:  Luke A Boralsky; Dagmara Marston; R David Grigg; John C Hershberger; Jennifer M Schomaker
Journal:  Org Lett       Date:  2011-03-25       Impact factor: 6.005

7.  Direct entry to erythronolides via a cyclic bis[allene].

Authors:  Kai Liu; Hiyun Kim; Partha Ghosh; Novruz G Akhmedov; Lawrence J Williams
Journal:  J Am Chem Soc       Date:  2011-09-06       Impact factor: 15.419

8.  Spirodiepoxide strategy to the C ring of pectenotoxin 4: synthesis of the C1-C19 sector.

Authors:  Sipak Joyasawal; Stephen D Lotesta; N G Akhmedov; Lawrence J Williams
Journal:  Org Lett       Date:  2010-03-05       Impact factor: 6.005

9.  Toward an integrated route to the vernonia allenes and related sesquiterpenoids.

Authors:  Da Xu; Michael A Drahl; Lawrence J Williams
Journal:  Beilstein J Org Chem       Date:  2011-07-05       Impact factor: 2.883

10.  Enantioselective Ruthenium-BINAP-Catalyzed Carbonyl Reductive Coupling of Alkoxyallenes: Convergent Construction of syn-sec,tert-Diols via (Z)-σ-Allylmetal Intermediates.

Authors:  Ming Xiang; Dana E Pfaffinger; Eliezer Ortiz; Gilmar A Brito; Michael J Krische
Journal:  J Am Chem Soc       Date:  2021-06-01       Impact factor: 16.383
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.