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Tetrahedron Letters

Volumn 19, Issue 22, 1978, Pages 1909-1912

A facile entry to pseudoguaianes. Total synthesis of damsinic acid

(2) Lansbury, Peter T a Serelis, Algirdas K a

a UNIVERSITY AT BUFFALO (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0008596677 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(01)94706-9 Document Type: Article

Times cited : (32)

References (21)

1
- 84918306511
- J. Romo,A. Romo^de Vivar,“Fortschritte der Chemie Organischen Naturstoffe”, 25, pp. 90-130.

2
- 0001596664
- Progress in Hydroazulene Synthesis
- (1972) Synthesis , pp. 517
- Marshall¹

3
- 0017069616
- (1976) J. Am. Chem. Soc. , vol.98 , pp. 3379
- Kretchmer¹ Thompson²

4
- 1542446388
- Total synthesis of (.+-.)-damsin
- (1977) The Journal of Organic Chemistry , vol.42 , pp. 3447
- De Clerq¹ Vanderwalle²

5
- 0017567493
- (1977) J. Am. Chem. Soc. , vol.99 , pp. 7393
- Grieco¹ Ohfune² Majetich³

6
- 0017300679
- (1976) J. Am. Chem. Soc. , vol.98 , pp. 4312
- Marshall¹ Ellison²

7
- 0014733221
- (1970) J. Org. Chem. , vol.35 , pp. 486
- Doskotch¹ Hufford²

8
- 0015915992
- Synthesis of Potential Ambra Odorants: 5,5,9-trimethyldecalyl derivatives
- (1973) Helvetica Chimica Acta , vol.56 , pp. 1414
- Ohloff¹ Naf² Decorzant³ Thommen⁴ Sundt⁵

9
- 33847804856
- (1974) J. Am. Chem. Soc. , vol.96 , pp. 3333
- Ireland¹ Lipinski² Kowalski³ Tilly⁴ Walba⁵

10
- 49549147598
- Stereospecific synthesis of d,l-cyclosativene. Alkyne capture of an homoallylic carbonium ion
- (1975) Tetrahedron Letters , pp. 1055
- Baldwin¹ Tomesch²

11
- 84918306510
- Satisfactory elemental analyses and confirmatory infrared, nmr and mass spectra were obtained for this compound.

12
- 0000391021
- (1972) J. Amer. Chem. Soc. , vol.94 , pp. 7210
- Corey¹ Beames²

13
- 84918306509
- 10 tetrasubstituted double bond could be slowly but stereospecifically reduced first before the otherwide more reactive acrylic ester side chain (cf. as in 7 → 9) reduces with less overall stereospecificity at both sites.

14
- 84918306508
- 4 was readily obtained in 25% overall yield from 1, without extensive purification of intermediates, a sequence which can probably be optimized in future work.

15
- 84918306507
- Some reduction of the carbonyl also occurred on occasion, thus necessitating careful “back oxidation” with pyridinium chlorochromate.

16
- 84914245589
- Novel cyclic carbene complexes of iron
- (1974) Journal of the American Chemical Society , vol.96 , pp. 1620
- Yamamoto¹

17
- 0003081702
- Reaction of lithio -butyl trimethylsilylacetate with aldehydes and ketones. A synthesis of α,β-unsaturated esters.
- (1974) Tetrahedron Letters , pp. 1403
- Hartzell¹ Sullivan² Rathke³

18
- 37049125603
- ?-Hydroxymethylation of ?- and ?-lactones: a new synthesis of ?-methylene-?-butyrolactones
- (1972) Journal of the Chemical Society, Chemical Communications , pp. 1317
- Grieco¹ Hiroi²

19
- 84918306506
- 7-epimer (cf. 7 → 9), which was fortunately not present in high enough concentration to obscure the clear-cut correspondence of the solution ir and nmr spectra of synthetic and natural methyl damsinate (or the acids).

20
- 84918306505
- These experiments were performed by J. E. Hengeveld; kinetic hydrolysis of the dienolate from 7, revealed the vinyl proton in 7a as a triplet (δ 5.69, J ⋍ 6 Hz).

21
- 84918306504
- Both 2-methyl-2-(β-chloroallyl)-1,3-cyclopentanedione and 2-methyl-2-allenyl-1,3-cyclopentanedione were also synthesized, via Claisen rearrangements of enol ethers, and cyclized to 3 in formic acid; initial yields are no better than those encountered with 1.

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