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ASYMMETRIC SYNTHESIS OF 6,7-EPOXYCITRONELLYLPIVALATE: OPTIMIZING THE SYNTHESIS OF THECALIFORNIA RED SCALE PHEROMONEbyJames Anthony MirandaA thesissubmitted in partialfulfillment of the requirements for the degree ofMaster of Science in Chemistryin the College of Science and MathematicsCalifornia State University, FresnoAugust 2001
Page 1: ABSTRACTASYMMETRIC SYNTHESIS OF 6,7
Page 5 and 6: APPROVED FOR FINAL DRAFT SUBMISSION
Page 7 and 8: AUTHORIZATION FOR REPRODUCTIONOF MA
Page 9 and 10: TABLE OF CONTENTSPageLIST OF FIGURE
Page 11 and 12: viii20. GC/MS trace of (3S) Citrone
Page 13 and 14: INTRODUCTIONAsymmetric Synthesis of
Page 15 and 16: 3a. Adult Female California Red Sca
Page 17 and 18: 5methyl-6-isopropenyl-3,9-decadien-
Page 19 and 20: 7created early in the total synthes
Page 21 and 22: 9manganese (III) chloride] is readi
Page 23 and 24: 11the particular alkene substrate.
Page 25 and 26: Figure 9. (R,R) Jacobsen’s cataly
Page 27 and 28: 15The starting material for our epo
Page 29 and 30: 17Figure 14. Partial radical forms
Page 31 and 32: 19used to characterize the asymmetr
Page 33 and 34: 21making a tertiary alcohol. The re
Page 35 and 36: 23order cuprate from Cu(CN) and R-L
Page 37 and 38: material showed that the alkene was
Page 39 and 40: Figure 19. GC/MS trace of [(3S,6RS)
Page 41 and 42: Figure 21. GC/MS trace of (3S,6RS)-
Page 43 and 44: Figure 23. IR spectrum of (3S,6RS)-
Page 47 and 48: Figure 26. GC/MS trace of (3S, 6RS)
Page 51 and 52: 39resolved, it was apparent that th
Page 53 and 54:
Figure 32. GC/MS trace of [(3S,6RS)
Page 55 and 56:
Figure 35. 13 C NMR spectrum of (3S
Page 57 and 58:
45Figure 37. 13 C NMR Spectrum of (
Page 59 and 60:
47Figure 39. 13 C NMR Spectrum of (
Page 61 and 62:
Figure 40. GC/MS trace of reaction
Page 63 and 64:
Page 65 and 66:
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550.336 ml), was added dropwise thr
Page 69 and 70:
Asymmetric Synthesis of (3S,6S)-6,7
Page 71 and 72:
temperature was allowed to rise slo
Page 73 and 74:
REFERENCES
Page 75:
6316. Houk, K.N.; DeMello, N.C.; Co
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