A new conversional synthesis of the ABC ring system of taxoids from the C19-diterpenoid alkaloid lycoctonine was developed in 6 steps with 2% overall yield. The distinctive features of the conversion include pinacol rearrangement, enlargement of ring B, and opening of a four-membered ring.
For recent reviews, see: (a) WangFP, ChenQH. (2010) The C19-dterpenoid alkaloids. In The Alkaloids: Chemistry and Biology, Vol.69, CordellGA (Ed.), Elsevier Science, USA. 1–577;
WangFP, LiZB, YangJS, LiBG. (1999) Modification of norditerpenoid alkaloids: II. A simple and convenient preparation of the imine derivatives of norditerpenoid alkaloids. Chinese Chemical Letters, 10, 453–456.
4.
WangFP, YangJS, ChenQH, YuL, LiBG. (2000) New access to 7,17-seco norditerpenoid alkaloids via reduction of the corresponding 8-chloro derivatives. Chemical & Pharmaceutical Bulletin, 48, 1912–1916.
5.
WangFP, ChenQH, LiZB, LiBG. (2001) Novel products from oxidation of the norditerpenoid alkaloid pseudaconine with HIO4. Chemical & Pharmaceutical Bulletin, 49, 689–694.
6.
WangFP, ChenQH, LiBG. (2001) Novel synthesis of 12,13-seconorditerpenoid alkaloids via semipinacol rearrangement and reaction with Br2-HOAc. Tetrahedron, 57, 4705–4712.
7.
XuL, ChenQH, WangFP. (2002) A novel skeletal rearrangement of the A ring of the immonium salt derived from norditerpenoid alkaloid yunaconitine. Tetrahedron, 58, 4267–4271.
8.
ChenQH, WangFP. (2002) Further studies on synthesis of the 12,13-seconorditerpenoid alkaloids. Chemical & Pharmaceutical Bulletin, 50, 1310–1317.
9.
ChenQH, XuL, WangFP. (2002) A novel conversion of norditerpenoid alkaloids into aconane-type diterpenes. Tetrahedron, 58, 9431–9444.
10.
ChenQH, XuL, WangFP. (2002) A new access to the cleavage of the N-19 bond of norditerpenoid alkaloids and their derivatives by formation of oxaziridines. Heterocycles, 57, 2357–2363.
11.
ChenQH, XuL, WangFP. (2003) Preparation of the N,19-seconorditerpenoid alkaloids from norditerpenoid alkaloid yunaconitine. Chinese Chemical Letters, 14, 147–150.
12.
ChenQH, WangFP. (2003) Further studies on the synthesis of 7,17-seco norditerpenoid alkaloids. Journal of Asian Natural Products Research, 5, 43–48.
13.
ShenXL, WangFP. (2004) New products from the reaction of acetyllycoctonine with N-bromosuccinimide (NBS). Chemical & Pharmaceutical Bulletin, 52, 1095–1097.
14.
WangFP, XuL. (2005) To seek an approach toward the chemical conversion of C19-diterpenoid alkaloids to taxoids. Tetrahedron, 61, 2149–2167.
15.
ShenXL, WangFP. (2005) mCPBA oxidation of acetyllycoctonine and its new products. Chemical & Pharmaceutical Bulletin, 53, 267–270.
16.
HeYM, ZouCL, ChenQH, WangFP. (2007) New formation of imines of C19-diterpenoid alkaloids by heating with DMSO. Journal of Asian Natural Products Research, 9, 713–720.
17.
ZouCL, LiuXY, WangFP, ChenQH. (2008) Two novel skeletal rearrangements involving in the C ring of C19-diterpenoid alkaloid deltaline derivatives. Chemical & Pharmaceutical Bulletin, 56, 250–253.
18.
ZouCL, JiH, XieGB, ChenDL, WangFP. (2008) An effective O-demethylation of some C19-diterpenoid alkaloids with HBr-glacial acetic acid. Journal of Asian Natural Products Research, 10, 1063–1067.
19.
ShenXL, ChenQH, WangFP. (2009) Further studies on CAB approach toward chemical conversion of C19-diterpenoid alkaloids to taxoids: synthesis of the vital intermediate C-nor-aconanone. Journal of Asian Natural Products Research, 11, 97–109.
20.
TangP, WangL, ChenQH, WangFP. (2011) Novel reactions of lycoctonine analogs: unusual pyrolysis of C4-COOH and hydrogenolysis of N-C6 bond. Tetrahedron, 67, 1076–1082.
21.
ZouCL, CaiL, JiH, XieGB, WangFP, JianXX, SongL, LiuXY, ChenDL, ChenQH. (2008) A novel approach to the taxane ABC ring system through chemical conversion from C19-diterpenoid alkaloid deltaline. Tetrahedron, 64, 7594–7604.
22.
SongL, ChenQH, SheXK, ChenXG, WangFP. (2011) Conversional synthesis and cytotoxic evaluation of novel taxoid analogs. Journal of Asian Natural Products Research, 13, 787–798.
23.
ShenXL, ChenQH, ChenDL, WangFP. (2009) Two novel aconane-type diterpenes derived from C-nor-C19-diterpenoid alkaloid. Chinese Chemical Letters, 20, 431–434.
24.
JiH, ChenQH, WangFP. (2009) A novel conversion of C19-diterpenoid alkaloids into aconane-type diterpenes with eight-membered ring system via skeletal rearrangement of corresponding diazonium derivatives. Chemical & Pharmaceutical Bulletin, 57, 233–239.
25.
WangFP, FanJZ, JianXX, LiBG. (1999) Modifications of norditerpenoid alkaloids. III. Preparation of 7,17-seco-yunaconitine derivatives via rearrangement of chloroamine. Chinese Chemical Letters, 10, 379–382.
26.
ChenQH, XuL, WangFP. (2002) A novel conversion of norditerpenoid alkaloids into aconane-type diterpenes. Tetrahedron, 58, 9431–9444.
27.
MarderR, DuboisJ, GuénardD, Guéritte-VoegeleinF, PotierP. (1995) Baccatin III derivatives: reduction of the C-11, C-12 double bond. Tetrahedron, 51, 1985–1994.
