Showing papers by "Philip Magnus published in 2000"
TL;DR: In this article, a variety of α,β-unsaturated ketones with Mn(dpm)3 (3 mol%)/PhSiH3 (1.3 equiv.)/isopropyl alcohol/O2, followed by reductive work-up with P(OEt)3 resulted in the formation of α-hydroxyketones.
99 citations
TL;DR: In this article, a variety of α,β-unsaturated ketones with Mn(dpm) 3 (3 mol%)/PhSiH 3 (1.3 equiv.)/isopropyl alcohol with the exclusion of air resulted in the formation of the saturated ketone.
66 citations
TL;DR: In this paper, Carvone has been converted into the sulfone 14 which comprises the left-hand side of the cytotoxic sesquiterpene, eleutherobin 1.
43 citations
TL;DR: In this paper, the key intermediate homoannular diene was converted into (±)-11,12-demethoxylahadinine via conjugate reduction and oxidation of 15 with Mn(dpm)2/PhSiH3/O2 at 0°C.
34 citations
TL;DR: Chlorination of the bisoxazole-indole 16 using N -chlorosuccinimide gave the dichloride 13 (86%) and the trichloride 12 (5%) thus completing the synthesis of the CDEF rings of diazonamide as discussed by the authors.
29 citations
TL;DR: In this paper, the synthesis of 6 comprising the CDG rings of the diazonamides was achieved in an overall yield of 75% from commercially available 3, 4.
29 citations
TL;DR: In this article, the synthesis of 6 comprising the CDG rings of the diazonamides was achieved in an overall yield of 75% from commercially available 3, 4.
Abstract: The synthesis of 6 comprising the CDG rings of the diazonamides was achieved in an overall yield of 75% from commercially available 3 .
3 citations
TL;DR: Chlorination of the bisoxazole-indole 16 using N -chlorosuccinimide gave the dichloride 13 (86%) and the trichloride 12 (5%) thus completing the synthesis of the CDEF rings of diazonamide as discussed by the authors.
Abstract: Chlorination of the bis-oxazole-indole 16 using N -chlorosuccinimide gave the dichloride 13 (86%) and the trichloride 12 (5%) thus completing the synthesis of the CDEF rings of diazonamide.
2 citations
TL;DR: In this paper, the key intermediate homoannular diene was converted into (±)-11,12-demethoxylahadinine via conjugate reduction and oxidation of 15 with Mn(dpm)2/PhSiH3/O2 at 0°C.
Abstract: The key intermediate homoannular diene 10 was converted into (±)-11,12-demethoxylahadinine 6 via the conjugate reduction and oxidation of 15 with Mn(dpm)2/PhSiH3/O2 at 0°C. Oxidation of 14 with PhI(OAc)2/MeOH followed by reduction gave 17, which was converted into (±)-kopsidasine 19 and kopsidasine-N-oxide 20. The structure of the latter was confirmed by comparison with an authentic sample, and by X-ray crystallography.
1 citations
TL;DR: In this paper, Carvone has been converted into the sulfone 14 which comprises the left-hand side of the cytotoxic sesquiterpene, eleutherobin 1.
Abstract: (+)-Carvone has been converted into the sulfone 14 which comprises the left-hand side of the cytotoxic sesquiterpene, eleutherobin 1 . Julia coupling of 14 to the aldehyde 21 , followed by oxidation, dissolving metal reduction and stereoselective reduction of the C8 carbonyl group resulted in 29 , which has the correct stereochemistry at C8 and C9. Further conversion of 29 into 37 , and attempted intramolecular cyclization resulted in fragmentation to the furan 39 and 38 . Asymmetric epoxidation of the allylic alcohols 42 and 48 resulted in neighboring group participation from the adjacent dimethoxy acetal and formation of the rearranged oxepane derivatives 44 , 45 and 49 , respectively.