Synthesis of a 2,9-dioxabicyclo[3.3.1]nonane via double intramolecular hetero-michael addition: Entry to the G-G ring system of the azaspiracids

Organic Letters

Volumn 3, Issue 7, 2001, Pages 979-982

  Aiguade, Josep ^a   Hao, Junliang ^a   Forsyth, Craig J ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,9 DIOXABICYCLO(3.3.1)NONANE; 2,9-DIOXABICYCLO(3.3.1)NONANE; ALKANE; AZASPIRACID; BICYCLO COMPOUND; MARINE TOXIN; NONANE; SPIRO COMPOUND; WATER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ISOMERISM; OXIDATION REDUCTION REACTION; SYNTHESIS;

ALKANES; BICYCLO COMPOUNDS; ISOMERISM; MARINE TOXINS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; SPIRO COMPOUNDS; WATER;

EID: 0035810370     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.5555/ol015556l     Document Type: Article

References (15)

1. Satake, M.; Ofuji, K.; Naoki, H.; James, K. J.; Furey, A.; McMahon, T.; Silke, J.; Yasumoto, T. J. Am. Chem. Soc. 1998, 120, 9967.
2. Ofuji, K.; Satake, M.; McMahon, T.; Silke, J.; James, K. J.; Naoki, H.; Oshima, Y.; Yasumoto, T. Nat. Toxins 1999, 7, 99.
3. Ito, E.; Satake, M.; Ofuji, K.; Kurita, N.; McMahon, T.; James, K.; Yasumoto, T. Toxicon 2000, 38, 917.
4. (a) Aiguade, J.; Hao, J.; Forsyth, C. J. Tetrahedron Lett. 2001, 42, 817.
5. (b) Hao, J.; Aiguade, J.; Forsyth, C. J. Tetrahedron Lett. 2001, 42, 821.
6. (c) Dounay, A. B.; Frosyth, C. J. Org. Lett. 2001, 3, 975.
7. (d) Carter, R. G.; Weldon, D. J. Org. Lett. 2000, 2, 3913.
8. Carbon numbering corresponds to that of 1-3.
9. The dehydration of dihydroxy ketones has been used previously to access 2,9-dioxabicyclo[3.3.1]nonane systems. See: Shimshock, S.; Watermire, R. E.; DeShong, P. J. Am. Chem. Soc. 1991, 113, 8791 and references therein.
10. Shono, K.; Ishifune, M.; Kashimura, S. Chem. Lett. 1990, 449.
11. Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
12. See Supporting Information for full experimental details.
13. A (Z)-enone analogue of 4 also failed to provide an HHMA product, presumably due to competitive hemiketalization of the enone carbonyl with the δ-hydroxyl group.
14. For a recent example of a double C-Michael addition upon an ynone, see: Grossman, R. B.; Varner, M. A.; Skaggs, A. J. J. Org. Chem. 1999, 64, 340.
15. Müller, S.; Liepold, B.; Roth, G. J.; Bestmann, H. J. Synlett 1996, 521.