Allylsilane-Based Annulations. Direct Stereoselective Syntheses Of (±)-Graveolide And (±)-Aromaticin

References

• This Work Was Presented At The 201st National Meeting Of The American Chemical Society In Atlanta, Ga, April, 1991 [Abstract Orgn #189]
   Google Scholar
• 1990 . Taken In Part From The Ms Thesis Of Stephen M. Condon, The University Of Georgia, And The Ph.D. Dissertation Of Jee-Seop Song, The University Of Georgia, 1991
   Google Scholar
• Author To Whom Correspondence Regarding These Syntheses Should Be Addressed
   Google Scholar
• Author To Whom Correspondence Regarding The X-Ray Crystallographic Study Of Lactone (19) Should Be Addressed
   Google Scholar
• Fleming , I. , Dunogues , J. and Smithers , R. 1989 . The Electrophilic Substitution Of Allysilanes And Vinylsilanes . Organic Reactions , 37 : 57 – 575 . For Recent Surveys Of Allylsilane Chemistry, See
   Google Scholar
• Majetich , G. 1989 . “ Allylsilanes In Organic Synthesis ” . In Organic Synthesis, Theory And Applications , Edited by: Hudlicky , T. 173 – 240 . Greenwich, Ct : Jai Press, Inc. .
   Google Scholar
• Appendino , G. , Calleri , M. , Chiari , G. , Gariboldi , P. and Menichini , F. 1986 . Structure Of Graveolide And Conformational Aspects Of Related Helenanolides . Gazzetta Chimica Italiana , 116 : 637 – 641 . Prior To Its Isolation From Natural Sources, Graveolide Was An Advanced Intermediate In Lansbury's Synthesis Of (±)-Aromaticin.5
   Google Scholar
• Lansbury , P. T. , David Hangauer , G. Jr. and Vacca , J. 1980 . Total Synthesis Of Pseudoguaianolides: (±)-Aromaticin And (±)-Aromatin . Journal Of The American Chemical Society , 102 : 3964 – 3965 .
   Web of Science ®Google Scholar
• Lansbury , P. T. and Hangauer , David G. Jr. 1981 . Total Synthesis Of Pseudoguaianolides-Ii . Tetrahedron , 37 : 371 – 378 .
   Web of Science ®Google Scholar
• Baraldi , P. G. , Barco , A. , Benetti , M. , Pollini , G. P. and Zanirato , V. 1984 . 2,3a,5,6,7a-Hexahydro-3H.,1H-Benzothiophene-3,4-Dione And Cyclopenta-[B]-Tetrahydrothiphene-3,4-Dione Enolate Anions As Synthetic Equivalents To Cyclohex-2-Enone And Cyclopent-2-Enone C-2 Carbanions . Tetrahedron Letters , 25 : 4291 For Examples Of The α-Alkylation Of Cycloalkenones
   Web of Science ®Google Scholar
• Smith , A. B. III , Branca , S. J. , Pills , N. N. and Guaciaro , M. A. 1982 . Stereocontrolled Total Synthesis Of (±)-Pentenomycins I-Iii, Their Epimers And Dehydropentenomycin I . Journal Of Organic Chemistry , 47 : 1869 – 1875 .
   Web of Science ®Google Scholar
• All Structures Drawn Herein Represent Racemates, Only One Enantiomer Being Drawn
   Google Scholar
• Reaction Conditions Have Not Been Optimized
   Google Scholar
• All Yields Are Isolated Yields
   Google Scholar
• Coupling Of The Lithio Reagent Derived From 2-Bromo-2-Cycloalken-1-One Ethylene Ketal (5)6b With (7) Gave Only The Desilylated Analogue Of (8) In Low Yield
   Google Scholar
• Trost , B. M. and Curran , D. 1981 . Synthesis Of D,L-Coriolin . Journal Of The American Chemical Society , 103 : 7380 – 7381 .
   Web of Science ®Google Scholar
• Majetich , G. , Leigh , A. J. and Condon , S. M. 1991 . Synthetic Applications Of Gilman Reagents Derived From 2-Bromo-2-Cyloalken-1-One Ethylene Ketals . Tetrahedron Letters , 32 : 605 – 608 .
   Web of Science ®Google Scholar
• Majetich , G. , Condon , S. , Hull , K. and Ahmad , S. 1989 . 1,3-Oxidative Rearrangements Of Dienols . Tetrahedron Letters , 30 : 1033 – 1036 .
   Web of Science ®Google Scholar
• Caine , D. 1976 . Reduction And Related Reactions Of α,β-Unsaturated Carbonyl Compounds With Metals In Liquid Ammonia . Organic Reactions , 23 : 1 – 253 .
   Google Scholar
• Pradhan , S. K. 1986 . Mechanism And Stereochemistry Of Alkai Metal Reductions Of Cyclic Saturated And Unsaturated Ketones In Protic Solvents . Tetrahedron , 42 : 6351 – 6388 .
   Web of Science ®Google Scholar
• Snider , B. S. and Cartaya-Marin , C. P. 1984 . A New Method For Cyclopentanone Annelation . Journal Of Organic Chemistry , 49 : 153 – 157 .
   Web of Science ®Google Scholar
• Snider , B. B. 1980 . Lewis Acid-Catalyzed Ene Reactions . Accounts Of Chemical Research , 13 : 426 – 432 .
   Web of Science ®Google Scholar
• Snider , B. B. , Rodini , D. J. , Kirk , T. C. and Cordova , R. 1982 . (1982) Dimethylaluminum Chloride Catalyzed Ene Reactions Of Aldehydes . Journal Of The American Chemical Society , 104 : 555 – 563 .
   Web of Science ®Google Scholar
• Lansbury , P. T. , Nickson , T. E. , Vacca , J. P. , Sindelar , R. D. and Messinger , J. M. II . 1987 . Total Synthesis Of Pseudoguaianolides V: 2,3-Dihydrofastigilin C . Tetrahedron , 43 : 5583 – 5594 .
   Web of Science ®Google Scholar
• Kretchmer , R. A. and Thompson , W. J. 1976 . The Total Synthesis Of (±)-Damsin . Journal Of The American Chemical Society , 98 : 3379 – 3380 .
   PubMed Web of Science ®Google Scholar
• Fried , J. and Sih , J. C. 1973 . “ Total Synthesis Of Prostaglandins. Control Of Regiospecificity In The Alane-Epoxide Reaction And Selective Catalytic Oxidation Of Alkynylation Products ” . In Tetrahedron Letters 3899
   Google Scholar
• Grieco , P. A. 1975 . Methods For The Synthesis Of α-Methylene Lactones . Synthesis , : 67 – 82 .
   Web of Science ®Google Scholar
• Gammill , R. B. , Wilson , C. A. and Bryson , T. A. 1975 . Synthesis Of α-Methylene-γ-Butyrolactones . Synthetic Communications , 56 : 245 – 268 .
   Web of Science ®Google Scholar
• Grieco , P. A. , Marinovic , N. and Miyashita , M. 1975 . Oxygenated α-Methylene-γ-Butyrolactones . Journal Of Organic Chemistry , 40 : 1670 – 1672 .
   Web of Science ®Google Scholar
• Grieco , P. A. , Ohfune , Y. and Majetich , G. 1977 . Stereospecific Total Synthesis Of (±)-Ambrosin, (±)-Damsin And (±)-Psilostachyin C . Journal Of The American Chemical Society , 99 : 7393 – 7395 .
   Web of Science ®Google Scholar