Stereoselective Synthesis of the Hydrophobic Side Chain of Scyphostatin

Ryukichi Takagi; Shinjiro Tsuyumine; Hiroko Nishitani; Wataru Miyanaga; Katsuo Ohkata

doi:10.1071/ch03298

Stereoselective Synthesis of the Hydrophobic Side Chain of Scyphostatin

Australian Journal of Chemistry ◽

10.1071/ch03298 ◽

2004 ◽

Vol 57 (5) ◽

pp. 439 ◽

Cited By ~ 13

Author(s):

Ryukichi Takagi ◽

Shinjiro Tsuyumine ◽

Hiroko Nishitani ◽

Wataru Miyanaga ◽

Katsuo Ohkata

Keyword(s):

Stereoselective Synthesis ◽

Side Chain ◽

Negishi Coupling ◽

Synthetic Pathway

The hydrophobic side chain of scyphostatin was synthesized by a convergent synthetic pathway. The key reactions were the enzymatic asymmetric acetylation of a meso-diol, construction of the C12′–C13′ trisubstituted E-olefin moiety by Negishi coupling, and construction of the (2′E,4′E ,E,6′E)-triene moiety by Horner–Wadsworth–Emmons olefination.

ChemInform Abstract: Highly Stereoselective Synthesis of Steroidal 22α-Allylic Alcohols via 22-Aldehydes and 1-Silyl-1-iodo-1-alkenes: A New Efficient Route to the Side Chain Construction of Brassinolide.

ChemInform ◽

10.1002/chin.199209275 ◽

2010 ◽

Vol 23 (9) ◽

pp. no-no

Author(s):

V. A. KHRIPACH ◽

V. N. ZHABINSKIY ◽

V. K. OLKHOVICK

Keyword(s):

Stereoselective Synthesis ◽

Side Chain ◽

Allylic Alcohols ◽

Efficient Route

Enantioselective synthesis of 1-aryl-2-propenylamines: a new approach to a stereoselective synthesis of the Taxol® side chain

Tetrahedron Asymmetry ◽

10.1016/j.tetasy.2004.01.035 ◽

2004 ◽

Vol 15 (6) ◽

pp. 941-949 ◽

Cited By ~ 24

Author(s):

Daniele Castagnolo ◽

Silvia Armaroli ◽

Federico Corelli ◽

Maurizio Botta

Keyword(s):

Stereoselective Synthesis ◽

Enantioselective Synthesis ◽

Side Chain ◽

New Approach

Stereoselective synthesis of side chain of glaucasterol using palladium (O) catalyst.

Tetrahedron ◽

10.1016/s0040-4020(01)87708-5 ◽

1987 ◽

Vol 43 (22) ◽

pp. 5315-5320 ◽

Cited By ~ 18

Author(s):

J.P. Genet ◽

J.M. Gaudin

Keyword(s):

Stereoselective Synthesis ◽

Side Chain

Stereoselective Synthesis of Cholesteryl Derivatives Bearing a Chiral Allenic Group in the Side Chain

Synthesis ◽

10.1055/s-1989-27161 ◽

1989 ◽

Vol 1989 (02) ◽

pp. 93-97 ◽

Cited By ~ 10

Author(s):

Alain Burger ◽

Charles Hetru ◽

Bang Luu

Keyword(s):

Stereoselective Synthesis ◽

Side Chain

A Practical and Stereoselective Synthesis of Taxol Side Chain

Synthetic Communications ◽

10.1081/scc-120016314 ◽

2003 ◽

Vol 33 (5) ◽

pp. 723-728 ◽

Cited By ~ 6

Author(s):

Zhongqiang Zhou ◽

Xingguo Mei

Keyword(s):

Stereoselective Synthesis ◽

Side Chain

ChemInform Abstract: STEREOSELECTIVE SYNTHESIS OF STEROID SIDE CHAIN: SYNTHESIS OF (2R,3R)-2-METHYL-3-((1R*)-1,5-DIMETHYLHEXYL)CYCLOPENTANONE

Chemischer Informationsdienst ◽

10.1002/chin.198546105 ◽

1985 ◽

Vol 16 (46) ◽

Author(s):

M. NAKAYAMA ◽

S. TANIMORI ◽

S. OHIRA

Keyword(s):

Stereoselective Synthesis ◽

Side Chain ◽

Chain Synthesis

ChemInform Abstract: Synthetic Studies Toward Phorboxazole A. Stereoselective Synthesis of the C28-C46 Side Chain Fragment.

ChemInform ◽

10.1002/chin.200101240 ◽

2001 ◽

Vol 32 (1) ◽

pp. no-no

Author(s):

David R. Williams ◽

Michael P. Clark ◽

Ulrich Emde ◽

Martin A. Berliner

Keyword(s):

Stereoselective Synthesis ◽

Side Chain ◽

Chain Fragment ◽

Phorboxazole A ◽

Synthetic Studies

ChemInform Abstract: Stereoselective Synthesis of Maitotoxin GHI-Ring System Having a 1,2-Diol Side Chain.

ChemInform ◽

10.1002/chin.200917206 ◽

2009 ◽

Vol 40 (17) ◽

Author(s):

Masanori Nagatomo ◽

Tadashi Nakata

Keyword(s):

Stereoselective Synthesis ◽

Ring System ◽

Side Chain

ChemInform Abstract: Direct, Stereoselective Synthesis of the Protected Paclitaxel (Taxol) Side Chain and High-Yield Transformation to Paclitaxel.

ChemInform ◽

10.1002/chin.199517190 ◽

2010 ◽

Vol 26 (17) ◽

pp. no-no

Author(s):

A. M. KANAZAWA ◽

J.-N. DENIS ◽

A. E. GREENE

Keyword(s):

Stereoselective Synthesis ◽

High Yield ◽

Side Chain

Approach Toward the Total Synthesis of Orevactaene. Part 2. Convergent and Stereoselective Synthesis of the C18—C31 Domain (I) of Orevactaene. Evidence for the Relative Configuration of the Side Chain.

ChemInform ◽

10.1002/chin.200302207 ◽

2003 ◽

Vol 34 (2) ◽

Author(s):

Michael G. Organ ◽

Yaroslav V. Bilokin ◽

Svetoslav Bratovanov

Keyword(s):

Total Synthesis ◽

Stereoselective Synthesis ◽

Side Chain ◽

Relative Configuration ◽

Domain I

Stereoselective Synthesis of the Hydrophobic Side Chain of Scyphostatin

ChemInform Abstract: Highly Stereoselective Synthesis of Steroidal 22α-Allylic Alcohols via 22-Aldehydes and 1-Silyl-1-iodo-1-alkenes: A New Efficient Route to the Side Chain Construction of Brassinolide.

Enantioselective synthesis of 1-aryl-2-propenylamines: a new approach to a stereoselective synthesis of the Taxol® side chain

Stereoselective synthesis of side chain of glaucasterol using palladium (O) catalyst.

Stereoselective Synthesis of Cholesteryl Derivatives Bearing a Chiral Allenic Group in the Side Chain

A Practical and Stereoselective Synthesis of Taxol Side Chain

ChemInform Abstract: STEREOSELECTIVE SYNTHESIS OF STEROID SIDE CHAIN: SYNTHESIS OF (2R*,3R*)-2-METHYL-3-((1R*)-1,5-DIMETHYLHEXYL)CYCLOPENTANONE

ChemInform Abstract: Synthetic Studies Toward Phorboxazole A. Stereoselective Synthesis of the C28-C46 Side Chain Fragment.

ChemInform Abstract: Stereoselective Synthesis of Maitotoxin GHI-Ring System Having a 1,2-Diol Side Chain.

ChemInform Abstract: Direct, Stereoselective Synthesis of the Protected Paclitaxel (Taxol) Side Chain and High-Yield Transformation to Paclitaxel.

Approach Toward the Total Synthesis of Orevactaene. Part 2. Convergent and Stereoselective Synthesis of the C18—C31 Domain (I) of Orevactaene. Evidence for the Relative Configuration of the Side Chain.

ChemInform Abstract: STEREOSELECTIVE SYNTHESIS OF STEROID SIDE CHAIN: SYNTHESIS OF (2R,3R)-2-METHYL-3-((1R*)-1,5-DIMETHYLHEXYL)CYCLOPENTANONE