ent-Kaurene全碳骨架中AB环系的不对称合成

doi:10.6023/cjoc202108029

摘要/Abstract

本课题组前期利用多样性导向合成策略完成ent-kaurene天然产物Xerophilusin I、Neolaxiflorin L、Eriocalyxin B、15-epi-Enmelol全合成工作, 为完成该类天然产物的不对称合成, 对Horner-Wadsworth-Emmons反应进行了优化, 改善了反应的区域选择性, 在酸性条件下后处理, 将Z/E混合物转化为单一Z构型. 基于温和的酸性条件实现了单一构型的转化, 提出了氢键辅助的Michael加成/retro-Michael消除的机理猜想. 发展了Cu(OTf)₂催化的不对称Diels-Alder反应: 以烯醇硅醚的双烯体3、β-酮酸酯1为亲双烯体, 在噁唑啉为手性配体的条件下, 以65%的收率和>19∶1 dr值完成AB环的构建.

关键词: ent-kaurene天然产物, Horner-Wadsworth-Emmons反应, 区域选择性, 不对称Diels-Alder反应

The total synthesis of ent-kaurene natural products of Xerophilusin I, Neolaxiflorin L, Eriocalyxin B, 15-epi- Enmelol completed by diversity-oriented synthesis strategy. In this paper, the regioselectivity of Horner-Wadsworth-Emmons reaction was optimized, and a single Z configuration was transformed from Z/E mixture under acidic condition. Based on the conversion of a single configuration under mild acidic conditions, a mechanism for hydrogen bond-assisted Michael addition/retro-Michael elimination is proposed. The asymmetric Diels-Alder reaction with silylenol ether dienyl 3 and β-ketoate 1 as dienophile was developed. Using Cu(OTf)₂ as Lewis acid and oxazoline as chiral ligand, AB-ring-skeleton was constructed with 65% yield and >19∶1 dr value.

Key words: ent-kaurane, Horner-Wadsworth-Emmons reaction, regioselectivity, asymmetric Diels-Alder reaction

引用此文

马文静, 朱礼志, 章梦珣, 李志成. ent-Kaurene全碳骨架中AB环系的不对称合成[J]. 有机化学, 2022, 42(2): 580-589.

Wenjing Ma, Lizhi Zhu, Mengxun Zhang, Chising Lee. Asymmetric Synthesis of AB Rings in ent-Kaurene Carbon Framework[J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 580-589.

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图/表 11

图1. 几种代表性的ent-kaurene天然产物

Figure 1. Several representative ent-kauranoids

图式1. 构建6,6,6,5-四环骨架的逆合成分析

Scheme 1. Retrosynthetic analysis of constructing 6,6,6,5-tetra- cyclic skeletons

图式2. 双烯体化合物3的手性合成

Scheme 2. Chiral synthesis of diene 3

Entry	Additive (equiv.)	Temp./℃	t/h	Z∶E
1	TEA (10.0)	r.t.	72	1∶2.5
2	2,6-Lutidine (10.0)	r.t.	72	1∶2.5
3	DABCO (10.0)	r.t.	72	1∶2.5
4	2,6-Lutidine (10.0)	Reflux	72	1∶10
5	1 mol/L HCl/THF (2.5)	r.t.	3	Single E

表1. HWE的Z/E混合产物转化为单一构型的尝试a

Table 1. An attempt to convert the Z/E mixture of HWE to a single configuration

图式3. 猜测酸性条件下Z式转化为E式的机理

Scheme 3. Proposed mechanism of the conversion from Z to E under acidic conditions

图式4. 双烯体的(R)-3和(S)-3的制备

Scheme 4. Synthesis of (R)-3 and (S)-3

图2. 噁唑啉配体的“静态位阻”R和“动态位阻”R'

Figure 2. “Static steric hindrance” R and “dynamic steric hindrance” R' of oxazoline ligands

Ligand	Yield^a/%	Recovery/% of 3	(+)-14a∶(–)-14b	exo/endo
L₁	33	40	1∶1.5	>10∶1
L₂	30	52	1∶3	>10∶1
L₃	67	31	2.5∶1	>10∶1
L₄	No reaction	70	—	—
L₅	32	50	1∶1	6∶1
L₆	65	27	5∶1	>10∶1
L₇	63	28	1∶ 2	8∶1
L₈	33	45	1.5∶1	>10∶1

表2. 不同的噁唑啉配体的筛选

Table 2. Screening of different oxazoline ligands

Entry	Solvent	Temp./℃	n(Lewis acid)∶n(ligand)	Cu(OTf)₂/mol%	Yield^a/% of (+)-14a	dr^b
1	Dichloromethane (DCM)	r.t.	1∶1.1	10	65	5∶1
2	1,2-Dichloroethane (DCE)	r.t.	1∶1.1	10	63	8∶1
3	Chlorobenzene	r.t.	1∶1.1	10	42	2.5∶1
4	1,2-Dichlorobenzene	r.t.	1∶1.1	10	48	3.5∶1
5	1,1,1-Trichloroethane	r.t.	1∶1.1	10	58	2.5∶1
6	Trichloromethane	r.t.	1∶1.1	10	43	3∶1
7	1,3-Dichloropropane	r.t.	1∶1.1	10	53	6∶1
8	DCE/toluene (V∶V=1∶1)	r.t.	1∶1.1	10	48	2.5∶1
9	DCE/toluene (V∶V=3∶1)	r.t.	1∶1.1	10	54	5∶1
10	DCE	r.t.	1∶1.5	10	65	13∶1
11	DCE	r.t.	1∶1.1	5	65	13∶1
12	DCE	r.t.	1∶1.1	1	—	—
13	DCE	0	1∶1.1	10	65	15∶1
14	DCE	0	1∶1.5	5	65	>19∶1

表3. 溶剂、温度、当量配比的筛选

Table 3. Screening of solvent, temperature, equivalent and ratio

图3. (+)-15a的单晶结构的确认

Figure 3. Confirmation of single crystal structure of (+)-15a

图式5. 化合物(–)-16a的手性合成

Scheme 5. Asymmetric synthesis of compound (–)-16a

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