Synthetic and computational studies on the ABC trioxadispiroketal subunit of the marine biotoxin azaspiracid-1

Natural Product Communications

Volumn 3, Issue 11, 2008, Pages 1771-1780

  Li, Jialiang ^a   Li, Xiaohua ^a   Mootoo, David R ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

Anomeric effect; Azaspiracid 1; DFT calculation; Spiroketal; Thermodynamic

Indexed keywords

AZASPIRACID; AZASPIRACID 1; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; DENSITY FUNCTIONAL THEORY; DIASTEREOISOMER; DRUG SYNTHESIS; NONHUMAN; OBSERVATION; STEREOCHEMISTRY; THERMODYNAMICS;

EID: 70349864934     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x0800301106     Document Type: Article

References (44)

1. Ofuji K, Satake M, McMahon T, Silke J, James KJ, Naoki H, Oshima Y, Yasumoto T. (1996) Two analogs of azaspiracid isolated from mussels, Mytilus edulis, involved in human intoxication in Ireland. Natural Toxins, 7, 99-102.
2. Ito E, Satake M, Ofuji K, Kurita N, McMahon T, James K, Yasumoto T. (2000) Multiple organ damage caused by a new toxin azaspiracid, isolated from mussels produced in Ireland. Toxicon, 38, 917-930. (Pubitemid 30084733)
3. Twiner MJ, Hess P, Dechraoui MB, McMahon T, Samonsa MS, Satake M, Yasumoto T, Ramsdell RS, Doucette GJ. Cytotoxic and cytoskeletal effects of azaspiracid-1 on mammalian cell lines. (2005) Toxicon, 45, 891-900. (Pubitemid 40719792)
4. (a) Nicolaou KC, Vyskocil S, Koftis VT, Yamada YMA, Ling T, Chen DY-K, Tang W, Petrovic G, Frederick MO, Satake YM. (2004) Structural revision and total synthesis of Azaspiracid-1, Part 1: Intelligence gathering and tentative proposal. Angewandte Chemie International Edition, 43, 4312-4318;
5. (b) Nicolaou KC, Koftis TV, Vyskocil S, Petrovic G, Ling T, Yamada YMA, Tang W, Frederick MO. (2004) Structural revision and total Synthesis of Azaspiracid-1, Part 2: Definition of the ABCD domain and total synthesis. Angewandte Chemie International Edition, 43, 4318-4324;
6. (c) Nicolaou KC, Pihko PM, Bernal F, Frederick MO, Qian W, Uesaka N, Diedrichs N, Hinrichs J, Koftis TV, Loizidou E, Petrovic G, Rodriquez M, Sarlah D, Zou N. (2006) Total synthesis and structural elucidation of Azaspiracid-1. Construction of key building blocks for originally proposed structure. Journal of the American Chemical Society, 128, 2244-2257;
7. (d) Nicolaou KC, Chen DY-K, Li Y, Uesaka N, Petrovic G, Koftis TV, Bernal F, Frederick MO, Govindasamy M, Ling T, Pihko PM, Tang W, Vyskocil S. (2006) Total synthesis and structural elucidation of Azaspiracid-1. Synthesis-based analysis of originally proposed structures and indication of their non-identity to the natural product. Journal of the American Chemical Society, 128, 2258-2267;
8. (e) Nicolaou KC, Koftis TV, Vyskocil S, Petrovic G, Tang W, Frederick MO, Chen DY-K, Li Y, Ling T, Yamada YMA. (2006) Total synthesis and structural elucidation of Azaspiracid-1. Final assignment and total synthesis of the correct structure of Azaspiracid-1. Journal of American Chemical Society, 128, 2859-2872;
9. (f) Nicolaou KC, Frederick MO, Petrovic G, Cole KP, Loizidou EZ. (2006) Total Synthesis and confirmation of the revised structures of Azaspiracid-2 and Azaspiracid-3. Angewandte Chemie International Edition, 45, 2609-2615.
10. (a) Evans DA, Kvoernø L, Mulder JA, Raymer B, Dunn TB, Beauchemin A, Olhava EJ, Juhl M, Kagechika K. (2007) Total synthesis of (+)-Azaspiracid-1. Part I: Synthesis of the fully elaborated ABCD aldehyde. Angewandte Chemie Internaitonl Edition, 46, 4693-4697;
11. (b) Evans DA, Dunn TB, Kvoernø L, Beauchemin A, Raymer B, Olhava EJ, Mulder JA, Juhl M, Kagechika K, Favor DA (2007) Total synthesis of (+)-Azaspiracid-1. Part II: Synthesis of the EFGHI sulfone and completion of the synthesis. Angewandte Chemie International Edition, 46, 4698-4703.
12. Li X, Li J, Mootoo DR. (2007) Synthesis of the ABCD trioxadispiroketal subunit of Azaspiracid-1: An iodoetherificationdehydroiodination strategy for complex spiroketals. Organic Letters, 9, 4303-4306.
13. (a) Carter RG, Weldon DJ. (2000) Studies directed toward the total synthesis of Azaspiracid: Stereoselective construction of C1-C12, C13-C19, and C21-C25 fragments. Organic Letters, 2, 3913-3916;
14. (b) Carter RG, Bourland TC, Graves DE. (2002) Synthesis of the ABC ring system of Azaspiracid. 1. Effect of D ring truncation on bis-spirocyclization. Organic Letters, 4, 2177-2179;
15. (c) Carter RG, Graves DE. (2001) Studies directed toward the total synthesis of azaspiracid. Construction of the C1-C19 carbon backbone and synthesis of the C10, C13 nonnatural transoidal bisspirocyclic ring system. Tetrahedron Letters, 42, 6035-6039;
16. (d) Carter RG, Bourland TC, Graves DE. (2002) Synthesis of the ABC ring system of Azaspiracid. 2. A Systematic study into the effect of C16 and C17 substitution on Bis-spirocyclization. Organic Letters, 4, 2177-2179 ;
17. (e) Carter RG, Graves DE, Gronemeyer MA, Bourland TC, Zhou X-T, Gronemeyer MA. (2003) Controlling influences in bisspiroketal formation: synthesis of the ABC ring system of azaspiracid. Tetrahedron, 59, 8963-8974.
18. (f) Zhou, XT, Carter RG. (2004) Synthesis of the ABCD and ABCDE ring systems of azaspiracid-1. Chemical Communications, 2138-2140;
19. (g) Zhou X-T, Carter RG. (2006) Synthesis of the C1-C26 northern portion of Azaspiracid-1: Kinetic versus thermodynamic control of the formation of the bis-spiroketal. Angewandte Chemie International Edition, 45, 1787-1790.
20. (a) Dounay AB, Forsyth CJ. (2001) Synthetic studies toward the C5-C20 domain of the Azaspiracids. Organic Letters, 3, 975-978;
21. (b) Aiguade J, Hao J, Forsyth CJ. (2001) Synthesis of a 2,9-dioxabicyclo[3.3.1]nonane via double intramolecular hetero-Michael addition: Entry to the F-G ring system of the Azaspiracids. Organic Letters, 3, 979-982;
22. (c) Forsyth CJ, Hao J, Aiguade J. (2001) Synthesis of the (+)-C26-C40 Domain of the Azaspiracids by a novel double intramolecular hetero-Michael addition strategy. Angewandte Chemie International Edition, 40, 3663-3667;
23. (d) Li Y, Zhou F, Forsyth CJ. (2007) Gold(I)-catalyzed bis-Spiroketalization: Synthesis of the trioxadispiroketal-containing A-D rings of Azaspiracid. Angewandte Chemie International Edition, 46, 279-282.
24. (a) Sasaki M, Iwamuro Y, Nemoto J, Oikawa M. (2003) Studies toward the total synthesis of azaspiracids: synthesis of the FGHI ring domain. Tetrahedron Letters, 44, 6199-6201; (Pubitemid 36897561)
25. (b) Ishikawa Y, Nishiyama S. (2004) Synthesis of the BCD ring system of azaspiracid: construction of the trispiro ring structure by the thioether approach. Tetrahedron Letters, 45, 351-354; (Pubitemid 37542277)
26. (c) Yadav JS, Joyasawal S, Dutta SK, Kunwar AC. (2007) Tetrahedron Letters, 48, 5335-5340;
27. (d) Oikawa M, Uehara T, Iwayama T, Sasaki M. (2006) Synthetic study of Azaspiracid-1: Synthesis of the EFGHI-ring fragment. Organic Letters, 8, 3943-394. (Pubitemid 44432826)
28. Deslongchamps P, Rowan DD, Pothier N, Sauve T, Saunders JK. (1991) Dioxaspiro[5.5]undecanes - An excellent system for the study of anomeric effects (anomeric and exoanomeric effects) in acetals. Canadian Journal of Chemistry, 59, 1105-1121.
29. For a review on bis-spiroacetals: Brimble MA, Furkert, DP. (2003) Chemistry of bis-spiroacetal systems: Natural products, synthesis and stereochemistry. Current Organic Chemistry, 7, 1461-1484.
30. The ABCD subunit with the natural bis-acetal configuration has also been generated directly from a diketone precursor under conditions that are more likely to be kinetic (ref. 4f).
31. For a related study on ABC trioxadispiroketal analogues, see ref. 7g
32. Zhu L, Mootoo DR. (2005) Synthesis of the non-classical acetogenin mucocin: a modular approach based on olefinic coupling reactions. Organic and Biomolecular Chemistry, 3, 2750-2754. (Pubitemid 41156395)
33. Schmid CR, Bryant RD, Dowlatzedan M, Philllips JL, Prather DE, Schantz RD, Sear NL, Vianco CS. (1991) Synthesis of 2,3-Oisopropylidene-D-glyceraldehyde in high chemical and optical purity: observations on the development of a practical bulk process. The Journal of Organic Chemistry, 56, 4056-4058.
34. 3 and its C(12) epimer. Journal of the American Chemical Society, 108, 2662-2674.
35. (a) Blakemore PR. (2002) The modified Julia olefination: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds. Journal of Chemical Society Perkin Transaction I, 2563-2585;
36. (b) Blakemore PR, Cole WJ, Kocienski PJ, Morley A. (1998) A Stereoselective synthesis of trans-1,2-disubstituted alkenes based on the condensation of aldehydes with metallated 1-phenyl-1H-tetrazol-5-yl sulfones. Synlett, 26-28;
37. (c) Baudin JB, Hareau G, Julia SA, Ruel O. (1991) A direct synthesis of olefins by reaction of carbonyl compounds with lithio derivatives of 2-[alkyl- or (2′-alkenyl)-or benzyl-sulfonyl]-benzothiazoles. Tetrahedron Letters, 32, 1175-1178.
38. The extent and even position of anomeric equilibra are known to vary with solvent: (a) Wiberg KB., Marquez M. (1994) The energy components of the anomeric effect for 2-methoxytetrahydropyran. An experimental comparison of the gas phase and solutions. The Journal of the American Chemical Society, 116, 2197-2198.
39. (b) Tvaroska I, Carver JP. (1998) The anomeric and exo-anomeric effects of a hydroxyl group and the stereochemistry of the hemiacetal linkage. Carbohydrate Research, 309, 1-9.
40. Wu A, Cremer, D. (2003) New approach for determining the conformational features of pseudorotating ring molecules utilizing calculated and measured NMR spin-spin coupling constants. Journal of Physical Chemistry A, 107, 1797-1810.
41. For other discussions on the interplay of stereoelectronic, steric and hydrogen bonding effects on the relative stability of bisspiroketal configurations: (a) Ishihara J, Sugimoto T, Murai A. (1998) Studies on the stability of 1,7,9- trioxadispiro[5,1.5.2]pentadecane system: The common tricyclic acetal moiety in pinnatoxin. Synlett, 603-606;
42. (b) Lu C, Zakarian A. (2007) Studies toward the synthesis of pinnatoxins: The B, C, D-dispiroketal fragment. Organic Letters, 9, 3161-3163.
43. Frisch MJ, Trucks GW, Schlegel, HB, Scuseria, GE, Robb, MA, Cheeseman JR, Montgomery JA, Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg J J, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PM, W.; Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. (2004) Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT.
44. For a recent computational study on trioxadispiroketals, see: Weldon AJ, Tschumper GS (2006) Energetics of oxaspirocycle prototypes: 1,7-Dioxaspiro[5.5] undecane and 1,7,9-trioxadispiro[5.1.5.3]hexadecane. The Journal of Organic Chemistry, 71, 9212-9216.